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Relevant bibliographies by topics / Cyclopentane derivatives

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Academic literature on the topic 'Cyclopentane derivatives'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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Journal articles on the topic "Cyclopentane derivatives"

1

Kotha, Sambasivarao, and Yellaiah Tangella. "Modular Approaches to Cyclopentanoids and their Heteroanalogs." Synlett 31, no. 20 (October 12, 2020): 1976–2012. http://dx.doi.org/10.1055/a-1288-8240.

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AbstractCyclopentanoids and their derivatives are interesting targets in synthetic organic chemistry due to their extensive applications in various branches of chemical sciences like pharmaceuticals, natural and non-natural products. In view of these applications, several synthetic strategies have been developed in the past three to four decades. In this article, we describe our work towards the synthesis of cyclopentanoids and their heteroanalogs involving diverse synthetic strategies during the past two decades. Among these, photo-thermal olefin metathesis, ring-closing metathesis, ring-rearrangement metathesis, cyclopentane annulation, [2+2+2] cycloaddition and Diels–Alder reactions have been used to assemble cyclopentane rings of diverse architecture. 1 Introduction 2 Synthesis of Spiro[4.4]nonane (A1) Derivatives 3 Synthesis of Octahydropentalene (A2) Derivatives 4 Synthesis of Linear Triquinanes (A3) 5 Synthesis Spiro Triquinanes (A4) 6 Synthesis of Angular Triquinane (A5) Systems 7 Synthesis of Hexahydro-2′H-spiro[cyclopentane-1,1′-pentalene] (A6) Ring System 8 Synthesis of Dispiro[4.1.47.25]tridecane (A7) Ring System 9 Synthesis of Hexahydro-1H-3a,7a-propanoindene Ring System10 Synthesis of Linear Tetraquinanes (A11 and A12)11 Synthesis of Tetrahydro-1′H,3′H-dispiro[cyclopentane-1,2′-pentalene-5′,1′′-cyclopentane] (A13) Ring System12 Synthesis of Decahydro-1H,8H-dicyclopenta[a,h]pentalene (A14) Ring System13 Synthesis of Dodecahydro-1H-dicyclopenta[a,d]pentalene (A15) Ring System14 Synthesis of Octahydro-1′H-spiro[cyclopentane-1,2′-cyclopenta[c]pentalene] (A16) Ring System15 Synthesis of Decahydrospiro[cyclopentane-1,7′-cyclopenta-[a]pentalene] (A17) Ring System16 Synthesis of Compact Tetraquinane (A18)17 Synthesis of Higher Polyquinanes18 Conclusions19 Acronyms

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2

Manna, Madhu Sudan, and Santanu Mukherjee. "Catalytic asymmetric desymmetrization approaches to enantioenriched cyclopentanes." Organic & Biomolecular Chemistry 13, no. 1 (2015): 18–24. http://dx.doi.org/10.1039/c4ob01649a.

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Asymmetric desymmetrization represents an excellent strategy for obtaining highly functionalized chiral building blocks. However, the application of this strategy for the synthesis of cyclopentane derivatives remained limited, when compared to cyclohexanes. Here, we give an overview of asymmetric desymmetrization reactions leading to enantioenriched cyclopentanes.

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3

Allan, RD, and J. Fong. "Synthesis of Analogs of GABA .15. Preparation and Resolution of Some Potent Cyclopentene and Cyclopentane Derivatives." Australian Journal of Chemistry 39, no. 6 (1986): 855. http://dx.doi.org/10.1071/ch9860855.

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A series of cyclopentene and cyclopentane analogues of GABA has been prepared utilizing a thermal cis -trans isomerization of the phthalimido β,γ -unsaturated acid (10) as the key step to obtain trans-4- aminocyclopent-2-ene-1-carboxylic acid (7). Resolution of some of the potent GABA analogues, in particular (+)-(4S)- and (-)-(4R)-4- aminocyclopent-1-ene-1-carboxylic acid (5), has been achieved by crystallization of isopropylideneribonolactone esters or pantolactone esters of the phthalimido -protected intermediates.

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4

KOJIMA, KOICHI, SHIGEO AMEMIYA, HIROSHI SUEMUNE, and KIYOSHI SAKAI. "Stereospecific synthesis of functionalized cyclopentane derivatives." CHEMICAL & PHARMACEUTICAL BULLETIN 33, no. 7 (1985): 2750–61. http://dx.doi.org/10.1248/cpb.33.2750.

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5

Kazakova, Oxana B., Elena V. Tretyakova, Irina E. Smirnova, Timur I. Nazyrov, Ol'ga S. Kukovinets, Genrikh A. Tolstikov, and Kiryll Yu Suponitskii. "An Efficient Oxyfunctionalization of Quinopimaric Acid Derivatives with Ozone." Natural Product Communications 8, no. 3 (March 2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800304.

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An access to oxyfunctionalized quinopimaric acid derivatives is reported. The ozonolysis of methyl dihydroquinopimarate occurs through 1,2-cycloaddition of ozone to the bridging double bond followed by intermolecular rearrangements and formation of nontrivial 4β-hydroxy-4α,14α-epoxy-13(15)-ene derivative 2. The oxidation of methyl furfurilydene dihydroquinopimarate with ozone led to anhydride 5 and unexpected carboxymethyl substituted cyclopentane lactone 6. The structure of compound 6 was confirmed by X-Ray analysis of its methyl ester.

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6

Campbell, M., DJ Collins, and AM James. "Synthesis of 2-(5',5'-Ethylenedioxy-1'-methylcyclopent-2'-en-1'-yl)ethanol, and Some 2H-Cyclopenta[b]furan Derivatives Formed by Intramolecular Displacement Reactions." Australian Journal of Chemistry 42, no. 1 (1989): 17. http://dx.doi.org/10.1071/ch9890017.

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Exchange dioxolanation of 2-methyl-2-(prop-2′-enyl)cyclopentane-1,3-done (1b) gave 3,3- ethylenedioxy-2-methyl-2-(prop-2′-enyl) cyclopentan-1-one (2) which, upon reduction and esterification , afforded the epimeric 3,3-ethylenedioxy-2-methyl-2-(prop-2′-enyl) cyclopent-1-yl benzoates (6d). Oxidative cleavage of the terminal double bond in (6d),followed by sodium borohydride reduction yielded 3,3-ethylenedioxy-2-(2'-hydroxyethyl)-2-methylcyclopent-1-yl benzoate (4b) which underwent acid- catalysed rearrangement to 6a-(2′-hydroxyethoxy)-3a- methylhexahydrocyclopenta [b]furan-4-yl benzoate (8b). Flash vacuum pyrolysis of the t- butyldimethylsilyl ether (12), derived from the hydroxy acetal (4b), afforded 3-[2′- (t- butyldimethylsilyloxy )ethyl]-4,4-ethy1enedioxy-3-methylcyclopent-1-ene (14) which upon selective cleavage of the silyl ether group gave 2-(5′,5′-ethylenedioxy-1′-methylcyclopent- 2'′en-1′-y1)ethanol (7). Reaction of the mesylate (16) of (7) with lithium bromide or iodide in tetrahydrofuran at 50-55� for several hours yielded some of the corresponding 3-(2′-haloethyl) compounds (17), but gave mainly the rearranged 6a-(2′-haloethoxy)-3a-methyl-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furans (19a) and (19b). Some related chemistry is described.

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7

Manchado, Alejandro, Victoria Elena Ramos, David Díez, and Narciso M. Garrido. "Multicomponent Domino Reaction in the Asymmetric Synthesis of Cyclopentan[c]pyran Core of Iridoid Natural Products." Molecules 25, no. 6 (March 13, 2020): 1308. http://dx.doi.org/10.3390/molecules25061308.

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The asymmetric synthesis of a compound with the cyclopentan[c]pyran core of iridoid natural products in four steps and 40% overall yield is reported. Our methodology includes a one-pot tandem domino reaction which provides a trisubstituted cyclopentane with five new completely determined stereocenters, which were determined through 2D homo and heteronuclear NMR and n.O.e. experiments on different compounds specially designed for this purpose, such as a dioxane obtained from a diol. Due to their pharmaceutical properties, including sedative, analgesic, anti-inflammatory, CNS depressor or anti-conceptive effects, this methodology to produce the abovementioned iridoid derivatives, is an interesting strategy in terms of new drug discovery as well as pharmaceutical development.

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8

Desai, Ranjit C., Peter Cicala, Laura C. Meurer, and Paul E. Finke. "Expeditious synthesis of tri-substituted cyclopentane derivatives." Tetrahedron Letters 43, no. 26 (May 2002): 4569–70. http://dx.doi.org/10.1016/s0040-4039(02)00901-2.

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9

Bauman, L. E., and J. Laane. "Pseudorotation of cyclopentane and its deuterated derivatives." Journal of Physical Chemistry 92, no. 5 (March 1988): 1040–51. http://dx.doi.org/10.1021/j100316a011.

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10

Lin, Yan, Qijun Wang, Yang Wu, Chang Wang, Hao Jia, Cheng Zhang, Jiaxing Huang, and Hongchao Guo. "Pd-catalyzed [3 + 2] cycloaddition of vinylcyclopropanes with 1-azadienes: synthesis of 4-cyclopentylbenzo[e][1,2,3]oxathiazine 2,2-dioxides." RSC Advances 8, no. 71 (2018): 40798–803. http://dx.doi.org/10.1039/c8ra08881k.

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Dissertations / Theses on the topic "Cyclopentane derivatives"

1

Clary, Heather Margaret Foster. "Synthesis and study of some cyclopentane-1,3-diyl derivatives as potentially long-lived singlet diradicals /." Thesis, Connect to this title online; UW restricted, 2003. http://hdl.handle.net/1773/8500.

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2

Chatah, Nour-El-Houda. "Apports de la cristallisation aux dédoublements d'espèces chirales." Rouen, 1996. http://www.theses.fr/1996ROUES032.

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Le comportement stéréospécifique des espèces organiques chirales impose le dédoublement du mélange racémique. La cristallisation fractionnée de sels diastéréoisomères est un protocole qui concerne près de 65 % des produits pharmaceutiques. L'intervention de l'agent chiral de dédoublement vérifiant la stoechiométrie pastorienne peut être fortement limitée en opérant en présence d'un agent achiral et réduisant ainsi le coût de la production. Le mélange en milieu éthanolique conduit à un système thermodynamique relevant d'un quaternaire réciproque. Le système met en jeu les (1R, 3S)-(+)-camphorates et les chlorhydrates des deux configurations de la fenfluramine. Une étude au refroidissement a permis d'observer et de quantifier les récoltes cristallines (monocamphorate droit de S(+) fenfluramine) avec une bonne pureté énantiomérique. Les recherches se sont étendues à l'identification et à la caractérisation des différents diastéréoisomères issus de mélanges racémiques entre l'amine et le diacide camphorique en milieu anhydre et en solution éthanolique. On a noté que l'anion disalifié perd son caractère stéréospécifique et ne reconnaît plus les deux configurations de l'amine. Enfin, les camphorates monosalifiés réalisent en milieu éthanolique une paire dite stable de sels énantiomères entre 56 et 25°C ; des essais de dédoublement par cristallisation préférentielle ouvrent une autre voie de dédoublement simultané de solutions doublement racémiques en acide et en base.

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3

Bernardes-Genisson, Vania. "Induction asymétrique dans la réaction intermoléculaire de Pauson-Khand et synthèse formelle de la (+)-brefeldine-A." Université Joseph Fourier (Grenoble ; 1971-2015), 1995. http://www.theses.fr/1995GRE10144.

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La réaction de Pauson-Khand, une cycloaddition entre un alcène, un alcyne et du monoxide de carbone représente l'une des méthodologies, mettant en jeu des métaux de transition, les plus efficaces pour préparer des cyclopentenones. L'emploi d'un auxiliaire de chiralite lie directement au partenaire acetylenique de cette réaction nous a permis, dans un premier temps, de développer une version asymétrique de la réaction intermoléculaire de pauson-khand. La réussite de cette stratégie a été possible grâce à la mise au point d'une méthode efficace et générale de préparation de complexes de cobalt d'ethers acétyléniques terminaux qui est basée sur l'utilisation d'un groupe silane comme élément protecteur de l'hydrogène acétylénique. Un travail initial d'évaluation des auxiliaires de chiralite, nous a permis d'élire le trans-deux-phenylcyclohexanol comme étant l'inducteur de choix dans notre cas. L'addition conjuguée hautement diastereoselective de réactifs organométalliques sur le cycloadduit enantiopur de Pauson-Khand, issu de la cyclisation avec le norbornadiene, nous a permis de développer une méthode de préparation enantioselective de cyclopentenones quatre-substituées, obtenues après réaction de retro diels-alder. Enfin, pour démontrer l'efficacité et l'importance de cette approche, nous avons réalisé une synthèse formelle enantioselective de la brefeldine-a naturelle, un macrolide intéressant pour ses activités immunodépressives

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4

Gumrukcu, Yasemin. "Synthesis Of 2-heteroaryl Substituted Chiral Fused Cyclopenta[c]pyridine Derivatives Via Pauson-khand Reaction." Master's thesis, METU, 2009. http://etd.lib.metu.edu.tr/upload/12611176/index.pdf.

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The racemic homoallylic and homopropargylic alcohol derivatives were resolved by applying chemoenzymatic method using various lipase type enzymes i.e., PS-C II, Lipozyme, CAL-B. The enantiomeric excess values of the resultant alcohols were determined by HPLC. These enantiomerically enriched homoallylic and homopropargylic alcohols were subjected to N-propargylation and N-allylation, respectively, by SN2 and modified Mitsunobu reactions. During the course of all reactions, stereochemistry of the chiral centers were under controlling according to the known reaction mechanisms. The resultant chiral N-tosylated enyne derivatives afforded the corresponding chiral fused cyclopenta[c]pyridinone derivatives (69, 73, 75 and 77) with acceptable chemical yields and excellent diastereoslectivity depending upon the conformational effect on the complete remote stereochemical control for the newly generated chiral centers. The chemoenzymatic applications done with biocatalysis (lipases) and the Pauson-Khand reaction are involved in &ldquo
Green Chemistry&rdquo
approach.

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5

Pingali, Aparna. "Synthesis and X-ray Diffraction Structures of 2-(2-thienylidene)-4,5-bis-(diphenylphosphino)-4-cyclopenten-1,3-dione and fac-BrRe(CO)3[2-(2-thienylidene)-4,5-bis(diphenylphosphino)-4-cyclopenten-1,3-dione]." Thesis, University of North Texas, 2005. https://digital.library.unt.edu/ark:/67531/metadc4942/.

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Treatment of 4,5 bis-(diphenylphosphino)-cyclopenten-1,3 dione with thiophene carboxyaldehyde in dichloromethane, in the presence of molecular sieves results in a new heterocyclic compound, 2-(2-thienylidene)-4,5-bis(diphenylphosphino)-4-cyclopenten-1,3-dione (ligand), with a high yield. This product was characterized by using both IR and NMR spectroscopic techniques and the solid-state structure of the ligand was determined using X-ray crystallography. When the ligand was treated with the solvent stabilized intermediate of ReBr(CO)5 with THF, a monomeric metal complex, fac-BrRe(CO)3[2-(2-thienylidene)-4,5-bis(diphenylphosphino)-4-cyclopenten-1,3-dione] was the result. The solid-state structure of the monomeric metal complex was determined using X-ray crystallography. Photolysis and thermolysis studies of the complex will be further explored.

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6

Han, Xiaoqing. "Synthesis of derivatives of 4H-cyclopenta[def]phenanthren-4-one and development of synthetic strategies for the polycyclic aromatic hydrocarbons with carbon frameworks represented on the surface of C₆₀." Morgantown, W. Va. : [West Virginia University Libraries], 2001. http://etd.wvu.edu/templates/showETD.cfm?recnum=2036.

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Thesis (M.S.)--West Virginia University, 2001.
Title from document title page. Document formatted into pages; contains ix, 41 p. : ill. Includes abstract. Includes bibliographical references (p. 39-41).

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7

Santos, Marilia Simão dos 1984. "A potencialidade sintética da reação de Morita-Baylis-Hillman explorada na síntese de compostos tricarbonilados vicinais e derivados ciclopenta[b]indólicos." [s.n.], 2012. http://repositorio.unicamp.br/jspui/handle/REPOSIP/250254.

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Orientador: Fernando Antônio Santos Coelho
Dissertação (mestrado) - Universidade Estadual de Campinas, Instituto de Química
Made available in DSpace on 2018-08-20T04:45:55Z (GMT). No. of bitstreams: 1 Santos_MariliaSimaodos_M.pdf: 8319783 bytes, checksum: b09561f94bf536402f8e5e21e0e6dc3c (MD5) Previous issue date: 2012
Resumo: A potenciabilidade sintética dos adutos de Morita-Baylis-Hillman foi explorada no desenvolvimento de uma nova estratégia para a preparação de compostos tricarbonilados vicinais e derivados ciclopenta[b]indólicos. Os compostos tricarbonilados vicinais representam um padrão estrutural de grande interesse sintético, pois são empregados na síntese de heterociclos e diversas moléculas com atividade biológica. A metodologia desenvolvida envolve três etapas que constituem na síntese do aduto de MBH e de duas oxidações subsequentes. A rota se mostrou rápida, simples e eficiente, com rendimentos globais variando entre 15-75%. Além da facilidade operacional essa estratégia é quimicamente sustentável já que apresenta um baixo nível de geração de resíduos químicos. Os núcleos ciclopenta[b]indólicos estão presentes na estrutura de diversos produtos naturais e moléculas bioativas, fato que se torna um estímulo para o desenvolvimento de novas rotas sintéticas. A estratégia baseia-se na oxidação do aduto de MBH seguida de adição de Michael utilizando indol. O produto gerado sofre redução e em seguida é ciclizado em meio ácido levando à obtenção do núcleo de interesse. A síntese se mostrou altamente diastereosseletiva e o mecanismo da etapa de ciclização foi investigado através de espectrometria de massas. Os compostos foram avaliados contra algumas linhagens de células tumorais exibindo atividade citótóxica promissora
Abstract: The synthetic potential of Morita-Baylis-Hillman adducts was exploited towards the development of a new strategy for the preparation of vicinal tricarbonyl compounds and cyclopenta [b] indole derivatives. The vicinal tricarbonyl compounds represent a structural pattern of great synthetic interest because they are employed in the synthesis of heterocycles and several biologically active compounds. The three steps methodology involves the the preparation of MBH adducts, followed by two subsequent oxidations. The route proved to be fast, simple and efficient, with overall yields ranging from 15 to 75%. This strategy is operationally ease and sustainable, since a low level of waste is generated. The nuclei cyclopenta [b]indoles are present in the structure of some natural products and bioactive compounds. This has stimulated efforts towards the development of new synthetic routes to prepare this heterocyclic pattern. Our strategy is based on the oxidation of MBH adduct followed by Michael addition using indole as nucleophile to provide a substituted b-ketoester. The keto carbonyl was reduced and the substituted b-hydroxyester was therefore cyclized in acid conditions leading the desired heterocycles. The synthesis was highly diastereoselectivity and mechanism of the cyclization step was monitored by mass spectrometry. The compounds were evaluated against some tumor cell lines exhibiting promising cytotoxic activity
Mestrado
Quimica Organica
Mestra em Química

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8

Chen, Kai-Han, and 陳楷涵. "Highly Enantioselective Synthesis of Cyclopentane from Newly Developed Coumarin Derivatives by Organocatalytic Asymmetric (3+2) Cyclization." Thesis, 2017. http://ndltd.ncl.edu.tw/handle/kefd2q.

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碩士
國立臺灣師範大學
化學系
105
Coumarin derivatives have the large biological activity, and in nature are also important natural product, therefore, how to make the addition on coumarin derivatives becomes a very important issue. In the past, we mostly construct five heteroatomed ring on the coumarin in asymmetric-organocatalyzed reaction. Nowadays, we use the newly developed coumarin derivatives as the substrates, and develope the great strategy to establish the five-carbon ring on the coumarin derivatives, and use the intermediates to figure out this reaction mechanism. In the second part, the synthesis of complex compounds in organic reactions usually requires the construction of the steps via the multi-step reaction step. However, due to the fact that the multi-step reaction is liable to the waste of resources, so research has become an important subject through the domimo reaction. This part focusing on the development of serial reaction initiation ideas and test results.

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9

Cheng-PeiYu and 余承霈. "Attempted Synthesis of Biradicaloid Polycyclic Aromatic Hydrocarbons：Zethrene Derivatives and Cyclopenta[def]fluorene Derivatives." Thesis, 2016. http://ndltd.ncl.edu.tw/handle/88498438082692400838.

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10

Sung, Shih-Ping, and 宋士平. "Study of Multicomponent Reaction Methodology Toward Synthesis of Multisubstituted Cyclopentenes and Isatin Derivatives." Thesis, 2015. http://ndltd.ncl.edu.tw/handle/8943y8.

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碩士
國立交通大學
應用化學系碩博士班
103
In this study, we used phosphine, (E)-dimethyl hex-2-en-4-ynedioate and benzylidenemalononitrile to obtain the dicyanocyclopentene bearing ylide functionality. We characterized these products by 1H, 13C, 31P, IR, Mass and X-ray diffraction analyses. These readily available structures may be adventageous to the total synthesis of molecules having this moiety. The other study, We obtained isatin- derivative bearing -ylide in one pot and characterized them by NMR, IR, MS and X-ray diffraction analyses. To optimize and discuss the effects substituent effects, we study reactions under different conditions and replace different reactants in this four-component reactions. Such synthetic methodology can be used to synthesize nature products because lots of nature compounds bear isatin skeleton.

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Books on the topic "Cyclopentane derivatives"

1

S, Bhatt Tarlochan, ed. Cyclopenta(a)phenanthrenes: Polycyclic aromatic compounds structurally related to steroids. Cambridge [Cambridgeshire]: Cambridge University Press, 1987.

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2

Coombs, Maurice M., and Tarlochan S. Bhatt. Cyclopenta[a]-phenanthrenes (Cambridge Monographs on Cancer Research). Cambridge University Press, 1987.

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Book chapters on the topic "Cyclopentane derivatives"

1

Chiang, P. C., and J. W. Bode. "Formal Homoenolate Additions to Enones: Synthesis of Cyclopentane Derivatives." In Lewis Base and Acid Catalysts, 1. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-204-00308.

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2

PITZER, KENNETH S., and WILM E. DONATH. "Conformations and Strain Energy of Cyclopentane and its Derivatives." In World Scientific Series in 20th Century Chemistry, 98–103. WORLD SCIENTIFIC, 1993. http://dx.doi.org/10.1142/9789812795960_0018.

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3

Taber, Douglass. "The Paquette Synthesis of Fomannosin." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0096.

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The compact sesquiterpene ( + )-fomannosin 3, isolated from the pathogenic fungus Fomes annonsus, presents an interesting set of challenges for the organic synthesis chemist, ranging from the strained cyclobutene to the easily epimerized cyclopentanone. In the synthesis of 3 developed (J. Org. Chem . 2008, 73, 4548) by Leo A. Paquette of Ohio State University, the cyclopentane was constructed by ring-closing metathesis of 1. The real challenge of the synthesis was the enantiospecific preparation of 1 from D-glucose. The starting point for the preparation of 1 was the glucose derivative 4. Selective acetonide hydrolysis followed by oxidative cleavage gave the ester 5, which on base treatment followed by hydrogenation delivered the endo ester 6. Condensation of the enolate of 6 with formaldehyde proceeded with high diastereoselectivity, to give, after protection, the ester 7. Conversion of the ester to the vinyl group, exposure to methanolic acid and ether formation completed the preparation of 9. The construction of the cyclobutane of 1 was effected by an interesting application of the Negishi reagent (Cp2ZrCl2/2 x BuLi). Complexation of Cp2Zr with the alkene followed by elimination generated an allylic organometallic 11, which added to the released aldehyde to give the cyclobutanes 12 and 13 in a 2.4:1 diastereomeric ratio. Homologation of the aldehyde 13 and subsequent oxidation were straightforward, but subsequent methylenation of the hindered carbonyl was not. At last, it was found that Peterson olefination worked well. Metathesis then delivered the cyclopentene 2. The last carbons of the skeleton were added by intramolecular aldol cyclization of the thioester 16. The seemingly simple task of converting the alkene of 17 into a ketone proved challenging. Eventually, dihydroxylation followed by oxidation, and then SmI2 reduction, completed the transformation. This still left the challenge of controlling the cyclopentane stereogenic center. Remarkably, dehydration and epimerization led to (+)-Fomannosin 3 as a single dominant diastereomer.

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4

Taber, Douglass. "Enantioselective Organocatalyzed Construction of Carbocyclic Rings." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0072.

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One of the most practical ways to construct enantiomerically-enriched carbocyclic systems is to effect asymmetric transformation of preformed prochiral rings. Choon-Hong Tan of the National University of Singapore observed (Chem. Commun. 2008, 5526) that allylic halides such as 1 coupled with malonates such as 2 to give the α-methylene ketone 3 in high ee. Xinmiao Liang of the Dalian Institute of Chemical Physics and Jinxing Ye of the East China University of Science and Technology reported (Chem. Commun. 2008, 3302) that nitromethane 5 could be added to enones such as 4 to construct cyclic quaternary stereogenic centers such as that of 6. The addition of the cyclohexanone 7 to the acceptor 8 described (Chem. Commun. 2008, 6315) by Yixin Lu, also of the National University of Singapore led to the creation of two new cyclic stereogenic centers. Polycarbocyclic prochiral rings are also of interest. Teck-Peng Loh of Nanyang Technological University devised (Tetrahedron Lett. 2008, 49, 5389) the steroid AB donor 10, that added to crotonaldehyde 1 to give the single enantiomerically-pure diastereomer 12. Nitro alkenes are excellent Michael acceptors. Dieter Enders of RWTH Aachen took advantage of this (Angew. Chem. Int. Ed. 2008, 47, 7539) in developing the addition of aldehydes such as 14 to the nitroalkene 13. Intramolecular alkylation ensued, to deliver the product 15 as a single diastereomer. Guofu Zhong, also of Nanyang Technological University, established (Organic Lett. 2008, 10, 3425; Organic Lett. 2008, 10, 3489) an approach to cyclopentane construction based on the Michael addition of β-ketoesters such as 16 and 19 to nitroalkenes such as 17 and 20. Intramolecular nitro aldol (Henry) addition led to 18, while an intramolecular Michael addition delivered 21. Damien Bonne and Jean Rodriguez of Aix-Marseille Université employed (Organic Lett. 2008, 10, 5409) intramolecular dipolar cycloaddition to convert the initial adduct between 22 and 23 to the cyclopentane 24. They also prepared cyclohexane derivatives using this approach. The diketone 25 is prochiral. Benjamin List of the Max-Planck Institut, Mülheim devised (Angew. Chem. Int. Ed. 2008, 47, 7656) an organocatalyst that mediated the intramolecular aldol cyclization of 25 to 26 in high ee.

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Taber, Douglass F. "Metal-Mediated C–C Ring Construction: The Carreira Synthesis of (+)-Asperolide C." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0073.

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Djamaladdin G. Musaev and Huw M. L. Davies of Emory University effected (Chem. Sci. 2013, 4, 2844) enantioselective cyclopropanation of ethyl acrylate 2 with the α-diazo ester 1 to give 3 in high ee. Philippe Compain of the Université de Strasbourg used (J. Org. Chem. 2013, 78, 6751) SmI2 to cyclize 4 to the cyclobutanol 5. Jianrong (Steve) Zhou of Nanyang Technological University effected (Chem. Commun. 2013, 49, 11758) enantioselective Heck addition of 7 to the prochiral ester 6 to give the cyclopentene 8. Liu-Zhu Gong of USTC, Hefei added (Org. Lett. 2013, 15, 3958) the Rh enolate from the enantioselective ring expansion of the α-diazo ester 9 to the nitroalkene 10, to give 11 in high de. Stephen P. Fletcher of the University of Oxford set (Angew. Chem. Int. Ed. 2013, 52, 7995) the cyclic quaternary center of 14 by the enantioselective conjugate addition to 12 of the alkyl zirconocene derived from 13. Alexandre Alexakis of the University of Geneva reported (Chem. Eur. J. 2013, 19, 15226) high ee from the conjugate addition of alkenyl Al reagents (not illustrated) to 12. Paultheo von Zezschwitz of Philipps-Universität Marburg prepared (Adv. Synth. Catal. 2013, 355, 2651) the silyl enol ether 17 by trapping the intermediate from the conjugate addition of 16 to 15. Stefan Bräse of the Karlsruhe Institute of Technology effected (Eur. J. Org. Chem. 2013, 7110) conjugate addition to the prochiral dienone 18 to give the highly substituted cyclohexenone 19. Ping Tian and Guo-Qiang Lin of the Shanghai Institute of Organic Chemistry cyclized (J. Am. Chem. Soc. 2013, 135, 11700) 20 to the kinetic, less stable epimer of the diketone 21. Rh-mediated intramolecular C–H insertion has been a powerful tool for the construction of cyclopentane derivatives. Douglass F. Taber of the University of Delaware found (J. Org. Chem. 2013, 78, 9772) that the Rh carbene derived from 22 was discriminating enough to target the more nucleophilic C–H bond, leading to the cyclohexanone 23. Kozo Shishido of the University of Tokushima observed (Org. Lett. 2013, 15, 3666) high diastereoselectivity in the intramolecular Heck cyclization of 24 to 25.

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Taber, Douglass F. "Organocatalyzed C–C Ring Construction: The Jørgenson Synthesis of (+)-Estrone." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0070.

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Ana Maria Faísca Phillips and Maria Teresa Barros of the Universidade Nova de Lisboa added (Eur. J. Org. Chem. 2014, 152) the bromo ester 1 to cinnamaldehyde 2 to give the cyclopropyl phosphonate 3 in high ee. Mukund P. Sibi and Jayaraman Sivaguru of North Dakota State University used (Angew. Chem. Int. Ed. 2014, 53, 5604) an organocatalyst to mediate the 2+2 photocycloaddition of 4, leading to 5. Shu-Li You of the Shanghai Institute of Organic Chemistry expanded (Org. Lett. 2014, 16, 1810) the four-membered ring of 6 to create the cyclopentanone 7 in high ee. Damien Bonne and Jean Rodriguez of Aix-Marseille Université condensed (Chem. Eur. J. 2014, 20, 410) the cyclopentanone 8 with 9 to give 10. Santanu Mukherjee of the Indian Institute of Science, Bangalore added (Chem. Sci. 2014, 5, 1627) the lactone 12 to the prochiral 11 to give 13 with remarkable diastereo- and enantiocontrol. Yixin Lu of the National University of Singapore constructed (Angew. Chem. Int. Ed. 2014, 53, 5643) the cyclopentene 16 by adding 14 to the allene 15. Efraim Reyes and Jose L. Vicario of the Universidad del País Vasco prepared (Chem. Eur. J. 2014, 20, 2145) the highly substituted cyclohexene 19 by combining 17 and 18. Maurizio Benaglia of the Università degli Studi di Milano added (Adv. Synth Catal. 2014, 356, 493) the ketone 20 to 21 to create the cyclohexanone 22. Ben W. Greatrex of the University of New England in Australia used (J. Org. Chem. 2014, 79, 5088) an organocatalyst to cyclize the symmetrical dialdehyde 23 to the α-hydroxy ketone 24. Dieter Enders of RWTH Aachen added (Org. Lett. 2014, 16, 2954) the β-keto ester 25 to 26 to give an intermediate that was further condensed with 27 to complete the preparation of 28. Eric N. Jacobsen of Harvard University prepared (Angew. Chem. Int. Ed. 2014, 53, 5912) the cycloheptenone 30 by the enantioselective intermolecular addition of the pyrylium salt derived from 29 to ethyl vinyl ether. Bor-Cherng Hong of the National Chung Cheng University initiated (Org. Lett. 2014, 16, 2724) the assembly of the steroid derivative 33 by the enantioselective addition of 32 to the unsaturated aldehyde 31.

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Taber, Douglass F. "Carbocyclic Ring Construction: The Nicolaou Synthesis of Myceliothermophin E." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0082.

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Nan Zheng of the University of Arkansas developed (Adv. Synth. Catal. 2014, 356, 2831) a Ru catalyst for the addition of an amino cyclopropane 1 to an alkyne 2 to give 3. The reaction proceeded with high regiocontrol, but only modest stereocontrol. Alain De Mesmaeker of Syngenta Crop Protection, Switzerland found (Tetrahedron Lett. 2014, 55, 6577) that the β,γ-unsaturated amide 4 worked particularly well as a precursor to the keteniminium that cyclized to give, after hydrolysis, the cyclobutanone 5. Baeyer–Villiger oxidation of 5 led to 5-deoxystrigol 6. David Tymann and Martin Hiersemann of the Technische Universität Dortmund have been exploring (Org. Lett. 2014, 16, 4062; Synthesis 2014, 46, 3110) the intramolecular carbonyl ene reaction as a tool for the assembly of highly substituted cyclopentanes, as in the conversion of 7 to 8. On oxidation, 8 was readily carried on to the alkene 9. James L. Leighton of Columbia University conceived (J. Am. Chem. Soc. 2014, 136, 9878) the cascade transformation of 10 to 12. Deprotonation/silylation set the stage for Claisen rearrangement to give 11. The subsequent Cope rearrangement is an equilibrium process, driven by the ring strain of 11. K. C. Nicolaou of Rice University described (Angew. Chem. Int. Ed. 2014, 53, 10970) the total synthesis of the cytotoxic tetramic acid derivative myceliothermophin E 15. A key step in the synthesis was the intramolecular Michael addition/ aldol condensation that converted 13 to 14.

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Conference papers on the topic "Cyclopentane derivatives"

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Lee, Te-Chang, Pei-Chih Lee, Rajesh Kakadiya, and Tsann-Long Su. "Abstract C31: Derivatives of 3a-aza-cyclopenta[a]indene effectively suppress the growth of P-glycoprotein overexpressing cells in in vitro and in vivo systems." In Abstracts: AACR-NCI-EORTC International Conference: Molecular Targets and Cancer Therapeutics--Nov 12-16, 2011; San Francisco, CA. American Association for Cancer Research, 2011. http://dx.doi.org/10.1158/1535-7163.targ-11-c31.

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