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Relevant bibliographies by topics / Asymmetric carbocycle synthesis

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Academic literature on the topic 'Asymmetric carbocycle synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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Journal articles on the topic "Asymmetric carbocycle synthesis"

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Xie, Xin, Wei Huang, Cheng Peng, and Bo Han. "Organocatalytic Asymmetric Synthesis of Six-Membered Carbocycle-Based Spiro Compounds." Advanced Synthesis & Catalysis 360, no. 2 (November 16, 2017): 194–228. http://dx.doi.org/10.1002/adsc.201700927.

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Schwarz, Jacob B., and A. I. Meyers. "Tandem α-Cyano Enamine/Enolate Alkylations on Bicyclic Lactams: Asymmetric Carbocycle and Heterocycle Synthesis." Journal of Organic Chemistry 63, no. 5 (March 1998): 1619–29. http://dx.doi.org/10.1021/jo971920b.

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Marcantonio, Enrico, Claudio Curti, Lucia Battistini, Andrea Sartori, Luana Cardinale, Giorgio Pelosi, and Franca Zanardi. "Direct, Asymmetric Synthesis of Carbocycle‐Fused Uracils via [4+2] Cycloadditions: a Noncovalent Organocatalysis Approach." Advanced Synthesis & Catalysis 363, no. 10 (March 31, 2021): 2625–33. http://dx.doi.org/10.1002/adsc.202100082.

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Bhuniya, Rajib, Tridib Mahapatra, and Samik Nanda. "Klebsiellapneumoniae (NBRC 3319) Mediated Asymmetric Reduction of α-Substituted β-Oxo Esters and Its Application to the Enantioiselective Synthesis of Small-Ring Carbocycle Derivatives." European Journal of Organic Chemistry 2012, no. 8 (January 30, 2012): 1597–602. http://dx.doi.org/10.1002/ejoc.201101695.

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Bhuniya, Rajib, Tridib Mahapatra, and Samik Nanda. "ChemInform Abstract: Klebsiella pneumoniae (NBRC 3319) Mediated Asymmetric Reduction of α-Substituted β-Oxo Esters and Its Application to the Enantioselective Synthesis of Small-Ring Carbocycle Derivatives." ChemInform 43, no. 30 (July 3, 2012): no. http://dx.doi.org/10.1002/chin.201230035.

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Ren, Qiao, Muyao Li, Lujiang Yuan, and Jian Wang. "Recent advances in N-heterocyclic carbene catalyzed achiral synthesis." Organic & Biomolecular Chemistry 15, no. 22 (2017): 4731–49. http://dx.doi.org/10.1039/c7ob00568g.

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This review reveals the recent developments in NHC-promoted non-asymmetric umpolung transformations resulting in the expeditious construction of versatile achiral natural heterocycles, carbocycles and acylated products.

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Meier, Chris, Simon Weising, and Ilaria Torquati. "Stereoselective Synthesis of 1′,2′-cis-Disubstituted Carbocyclic ribo-Nucleoside Analogues." Synthesis 50, no. 06 (December 20, 2017): 1264–74. http://dx.doi.org/10.1055/s-0036-1591732.

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Herein we disclose an efficient strategy for the convergent synthesis of 1′,2′-cis-disubstituted carbocyclic ribo-nucleoside analogues. Starting from an enantiomerically pure cyclopentenol precursor, the key step for the preparation of the highly functionalized carbocyclic building block is an asymmetric dihydroxylation. Employing different variants of the Mitsunobu protocol, the condensation with all-natural nucleobases or their precursors affords a series of ribo-configured carbocyclic 1′,2′-cis-disubstituted nucleoside analogues.

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Schneider, Lisa M., Volker M. Schmiedel, Tommaso Pecchioli, Dieter Lentz, Christian Merten, and Mathias Christmann. "Asymmetric Synthesis of Carbocyclic Propellanes." Organic Letters 19, no. 9 (April 26, 2017): 2310–13. http://dx.doi.org/10.1021/acs.orglett.7b00836.

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Hanessian, Stephen, Andrew M. Griffin, and Louis-David Cantin. "Asymmetric synthesis of functionalized carbocycles and heterocycles." Chirality 12, no. 5-6 (2000): 342–45. http://dx.doi.org/10.1002/(sici)1520-636x(2000)12:5/6<342::aid-chir7>3.0.co;2-y.

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Zhao, Y. F., M. G. Lee, T. F. Yang, B. K. Chun, J. F. Du, R. F. Schinazi, and C. K. Chu. "Asymmetric Synthesis of Cyclopropyl Carbocyclic Nucleosides." Nucleosides, Nucleotides and Nucleic Acids 14, no. 3 (May 1, 1995): 303–5. http://dx.doi.org/10.1080/15257779508012367.

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Dissertations / Theses on the topic "Asymmetric carbocycle synthesis"

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Haraguchi, Ryosuke. "Studies on Preparation of Functionalized Organozinc Reagents via Zinciomethylation." 京都大学 (Kyoto University), 2016. http://hdl.handle.net/2433/215552.

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Finniear, Aled. "Asymmetric synthesis of chiral carbocyclic nucleosides." Thesis, University of Nottingham, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.283609.

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Nimkar, Kalpana Sandeep. "Studies in asymmetric synthesis: Diastereoselective manipulations of conformationally anchored heterocycles and carbocycles." Diss., The University of Arizona, 1994. http://hdl.handle.net/10150/186994.

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The research, to be presented in two chapters discusses the development of new methods in asymmetric synthesis which may be applicable to the total synthesis of natural products. Chapter 1. We have developed the methodology to functionalize heterocycles such as tetrahydropyran and tetrahydrofuran using intermolecular diastereoselective radical trapping reactions. This method was also extended to prepare bicyclic acetals with three chiral centers using intramolecular radical reactions. The stereocontrol in both intermolecular and intramolecular reactions was studied. This methodology may be developed further to synthesize deoxygenated and substituted carbohydrates. Chapter 2. The highly functionalized eight membered carbocycle is the basic structural unit of many natural products of biological interest. The methodology developed and presented in this chapter utilizes chiral cyclopropyl ketals of eight member carbocycle and introduces functionalities on the eight membered ring with good stereocontrol. This methodology has direct application in the synthesis of many natural products containing functionalized eight member carbocycles.

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Deiana, Luca. "Development of Catalytic Enantioselective Approaches for the Synthesis of Carbocycles and Heterocycles." Doctoral thesis, Stockholms universitet, Institutionen för organisk kemi, 2013. http://urn.kb.se/resolve?urn=urn:nbn:se:su:diva-94680.

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In biological systems, most of the active organic molecules are chiral. Some of the main constituents of living organisms are amino acids and sugars. They exist predominantly in only one enantiomerically pure form. For example, our proteins are built-up by L-amino acids and as a consequence they are enatiomerically pure and will interact in different ways with enantiomers of chiral molecules. Indeed, different enantiomers or diastereomers of a molecule could often have a drastically different biological activity. It is of paramount importance in organic synthesis to develop new routes to control and direct the stereochemical outcome of reactions. The aim of this thesis is to investigate new protocols for the synthesis of complex chiral molecules using simple, environmentally friendly proline-based organocatalysts. We have investigated, the aziridination of linear and branched enals, the stereoselective synthesis of β-amino acids with a carbene co-catalyst, the synthesis of pyrazolidines, the combination of heterogeneous transition metal catalysis and amine catalysis to deliver cyclopentenes bearing an all-carbon quaternary stereocenter and a new heterogeneous dual catalyst system for the carbocyclization of enals. The reactions presented in this thesis afforded the corresponding products with high levels of chemo-, diastero- and enantioselectivity.

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 5: Submitted.

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Cotterill, Ian Charles. "Lipase catalyzed kinetic resolution and the asymmetric synthesis of carbocyclic oxetanocin A." Thesis, University of Exeter, 1992. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.317336.

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Docherty, Paul Henry. "Diastereocontrolled synthesis of hetero- and carbocycles via manganese(III) and copper(II) : towards a novel prostaglandin total synthesis." Thesis, University of Oxford, 2008. http://ora.ox.ac.uk/objects/uuid:6ca5556a-3d2d-454a-abbd-0a3a269c5724.

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The prostaglandins are a unique family of natural products found in all mammalian life, including humans. Their biological significance is profound, and they are responsible for a vast array of bodily functions. This importance, coupled with their low concentration in vivo, has made them attractive targets for total chemical synthesis. The work herein describes synthetic efforts towards their synthesis using an oxidative radical cyclisation to construct the key [3.3.0]-bridged bicyclic lactone, from which the prostaglandin skeleton may be derived. Key to this was the development of manganese(III) acetate and copper(II) triflate as optimal reagents for this cyclisation of unsaturated malonate/malonic acid derivatives. To study this, several model substrates for this crucial cyclisation were synthesised, and their cyclisation analysed. Chapter 5 describes the design and synthesis of several model substrates containing malonate groups for the oxidative radical cyclisation. The results of the cyclisation with manganese(III) and various copper(II) salts influenced the design of the substrates, and led to the use of malonic acids as more effective substrates for the formation of [3.3.0]-bicyclic lactones. A catalytic process, in which atmospheric oxygen is the terminal oxidant was also developed. Chapter 6 describes the studies towards a total synthesis of the prostaglandin family. Two potential routes are followed, the first of which used a key asymmetric epoxidation to install asymmetry. A Suzuki coupling was used to deliver the desired diene required for the cyclisation substrate, which was successfully cyclised using manganese(III) acetate and copper(II) triflate, creating the desired [3.3.0]-bicyclic lactone in good yield and with excellent diastereomeric control. A second, shorter route to the same lactone was also developed, using a novel asymmetric deconjugative aldol condensation to establish asymmetry. Cyclisation of this analogous substrate was also successful, delivering the same lactone after olefin metathesis.

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Shuttleworth, Stephen Joseph. "Approaches to the asymmetric synthesis of substituted carbocycles using the 1,3-dithiane 1-oxide (DiTOX) building block." Thesis, University of Liverpool, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.241457.

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Dange, Nitin Shivaji, and 丹尼丁. "Development Of Innovative Organocatalytic Reaction Methods For The Asymmetric Synthesis Of Highly Functionalized Carbocycles And Heterocycles." Thesis, 2012. http://ndltd.ncl.edu.tw/handle/68762685067579243805.

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博士
國立中正大學
化學暨生物化學研究所
100
This thesis accumulates our innovation in the field of asymmetric organocatalysis via sequential, cascade and one-pot reaction strategies. Second chapter introduces the first sequential organocatalytic Stetter and Michael-Aldol condensation reaction with certain evidence of kinetic asymmetric transformation. This reaction provides a simple and direct method for the stereoselective and enantioselective construction of fully functionalized cyclopentene derivatives with three contiguous chiral centers. The structures as well as the absolute configurations of adducts 51 were confirmed by X-ray analysis. Third chapter introduces unprecedented organocatalytic sequential Stetter and Michael-Aldol reaction. Synthesis of cyclopentane ring with all five-carbon stereocenters and tertiary alcohol quaternary stereocenter utilizing dynamic kinetic symmetric transformation. The introduction of an intramolecular H-bonding strategy in this system for increasing the yields of Stetter product, enabling DYKAT in Michael-Aldol reaction and obtaining a stable β-hydroxyaldehyde is especially distinguished features of this methodology. The structures as well as the absolute configurations of adducts 58 and 59 were confirmed by X-ray analysis. Forth chapter introduces organocatalytic one-pot Michael-Knoevenagel condensation-hetero-Diels-Alder reaction capable of synthesizing a variety of isochromene pyrimidinedione derivatives 68 bearing five stereocenters with excellent diastereoselectivity and enantioselectivities (up to 99 %). One-pot four consecutive reactions via organocatalysis provide an ecological and economical protocol. Excellent diastereoselectivities in intramolecular hetero-Diels-Alder reaction by a remote stereogenic center generated in situ via organocatalysis is a key feature and excellent strategy of this methodology. X-ray analysis of the appropriate adducts (80a, 80b and 79) confirm the structure and absolute configurations of the isochromene pyrimidinedione derivatives.

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Morris, Kay A. "Applications of B-Lactones: Utility of Spiroepoxy-B-Lactones and Development of a Double Diastereoselective Nucleophile Catalyzed, Aldol-Lactonization Process Leading to !-Lactone Fused Carbocycles and Tetrahydrofurans." Thesis, 2010. http://hdl.handle.net/1969.1/ETD-TAMU-2010-08-8405.

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Natural products continue to inspire synthetic chemists to develop novel methodologies to provide efficient and expedient syntheses of the target molecules. Haterumalide NA aroused our interest and prompted development of four differing methodologies. Three of the strategies pursued involved use of B-lactone scaffolds as intermediates. Extensions of the nucleophile catalyzed, aldol-lactonization (NCAL) reaction were also pursued and targeted toward alternative natural product targets. The reactivity of the unexpectedly stable strained spirocycle, spiroepoxy-B- lactone, was explored. Spiroepoxy-B-lactones exhibited a wide range of reactivity, but largely rearranged to tetronic acids. The desired reaction manifold remained inaccessible and led to application of the NCAL process to tetrahydrofuran-fused B-lactones. Several tetrahydrofuran-fused B-lactones were prepared, which displayed low diastereoselectivity. The diastereoselectivity could be somewhat improved in a double diastereoselective NCAL process with varied solvent systems, yet the carbocyclic analogues gave much more promising results. The use of carbocycle-fused !-lactones ultimately culminated in a double diastereoselective NCAL process, and overall led to improvements in diastereoselectivities from 1:1-2 up to >19:1. Further expansion of the substrate scope for the NCAL process was studied for application to bridged tricyclic B- lactones, access to carbocycle-fused y-lactones, and towards development of a dynamic kinetic resolution NCAL process. With our interest aimed at haterumalide NA, a modified Negishi cross coupling between zincates and dichloroolefins was also revisited. The stringent anhydrous reaction conditions led to reexamination of initial leads, which provided user-friendly anhydrous conditions by utilizing commercially available anhydrous solvent. However, application was implemented solely to a simplified model system.

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Lejkowski, Michal [Verfasser]. "Asymmetric synthesis of medium-sized carbocycles, spirocycles and oxabicycles via ring closing metathesis of sulfoximine substituted trienes and dihydropyran derivatives / vorgelegt von Michal Lejkowski." 2008. http://d-nb.info/992062527/34.

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Book chapters on the topic "Asymmetric carbocycle synthesis"

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Taber, Douglass F. "Chloranthalactone (Liu), Rumphellaone A (Kuwahara), Lactiflorin (Bach), Echinosporin (Hale), Harveynone (Taylor), (6,7-deoxy)-Yuanhuapin (Wender)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0082.

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The lindenane sesquiterpenes, exemplified by chloranthalactone 4, display interesting physiological activity. Bo Liu of Sichuan University assembled (Organic Lett. 2011, 13, 5406) 4 by opening the epoxide 1 to the carbene, which cyclized to 3. Establishment of the relative configuration of sidechain stereogenic centers is a continuing issue in carbocyclic synthesis. Shigefumi Kuwahara of Tohoku University paired (Tetrahedron Lett. 2012, 53, 705) Sharpless epoxidation, to prepare 5, with the Stork epoxy nitrile cyclization, leading to (+)-rumphellaone A 7. Three competing structures had been put forward for the structure of (+)-lactiflorin 10. Thorsten Bach of the Technische Universität München settled (Angew. Chem. Int. Ed. 2012, 51, 1261) this controversy by preparing the most likely structure, 10, and showing that it was congruent with the natural product. A key step in the synthesis was the tethered 2+2 cycloaddition of 8 to give 9. The conversion of a carbohydrate to a carbocycle is a powerful strategy for the enantiospecific construction of natural products. En route to (–)-echinosporin 14, Karl J. Hale of Queen’s University Belfast added (Org. Lett. 2012, 14, 3024) the allene 12 to the enone 11, prepared from glucose, to give the cyclopentene 13. Richard J.K. Taylor of the University of York prepared (Tetrahedron Lett. 2010, 51, 6619) the enone 16 by oxidation of m-iodophenol 15 followed by asymmetric epoxidation. Reduction followed by deprotection and Pd-mediated coupling delivered (–)-harveynone 17. Some of the daphnane diterpene orthoesters, exemplified by (6,7-deoxy)-yuanhuapin 20, are single-digit nanomolar inhibitors of protein kinase C. Paul A. Wender of Stanford University, in the course of initial studies to optimize this remarkable activity, prepared (Nature Chem. 2011, 3, 615) 20 by way of the thermal cyclization of 18 to 19.

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"Asymmetric Transformation of Prochiral Carbocyclic Rings." In Organic Synthesis, 204–5. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2006. http://dx.doi.org/10.1002/0470056312.ch103.

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Makida, Yusuke, and Ryoichi Kuwano. "Asymmetric Hydrogenation of Aromatic Carbocycles." In Kinetic Control in Synthesis and Self-Assembly, 97–108. Elsevier, 2019. http://dx.doi.org/10.1016/b978-0-12-812126-9.00005-5.

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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 Carbocyclic Construction:The Kobayashi Synthesis of (+)-Fomitellic Acid B." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0073.

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Jin K. Cha of Wayne State University described (J. Org. Chem. 2009, 74, 5528) the diastereoselective intramolecular cyclopropanation of nitriles with homoallylic alcohols such as 1 . Valery V. Fokin of Scripps/La Jolla found (J. Am. Chem. Soc. 2009, 131, 18034) that the diazoimine derived from 4 could add with high enantioselectivity to aryl alkenes, including styrene 5. Andreas Gansäuer of the University of Bonn optimized (Angew. Chem. Int. Ed. 2009, 48 , 8882; Tetrahedron 2009, 65, 10791) the Ti catalyst to enable efficient cyclization of substrates such as 7 to the corresponding cyclobutanes. F. Dean Toste of the University of California, Berkeley, devised (J. Am. Chem. Soc. 2009, 131, 9178) a gold catalyst for the enantioselective ring expansion of a prochiral allene such as 9 to the cyclobutanone 10. David J. Procter of the University of Manchester developed (J. Am. Chem. Soc. 2009, 131, 15467) the SmI2 -mediated cyclization of a lactone such as 11 to the cyclopentanone 12. Shigeki Matsunaga and Masakatsu Shibasaki of the University of Tokyo designed (Chem. Commun. 2009, 5138) a Ni catalyst for the enantioselective condensation of 13 with formaldehyde. Some acyclic β-keto esters could also be hydroxymethylated with high enantiocontrol. Darren J. Dixon, also of the University of Manchester, devised (J. Am. Chem. Soc. 2009, 131, 9140) a Cu catalyst for the enantioselective Conia cyclization of 15 to 16 . K. C. Nicolaou, also of Scripps/La Jolla, reported (Angew. Chem. Int. Ed. 2009, 48, 6293) a Rh catalyst for the related cyclization of 17 to 18. Ryo Shintani and Tamio Hayashi of Kyoto University showed (J. Am. Chem. Soc. 2009, 131, 13588) that a Rh catalyst could effect enantioselective conjugate addition of a tetraaryl borate even to a 3-methyl cyclohexenone 19, to establish the cyclic quaternary center. Alexandre Alexakis of the University of Geneva established (Chem. Commun . 2009, 3868) that with the easily ionized allylic bromide 21, Cu-mediated coupling with the alkyl Grignard 22 proceeded with substantial asymmetric induction. Jon D. Rainier of the University of Utah devised (Organic Lett. 2009, 11, 38774) conditions for effecting Ti-mediated intramolecular metathesis between an alkene and a lactam carbonyl, giving the cyclic enamide 24.

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Taber, Douglass. "Transition Metal-Mediated Construction of Carbocycles: Dimethyl Gloiosiphone A (Takahashi), Pasteurestin A (Mulzer), and Pentalenene (Fox)." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0074.

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There continue to be new developments in transition metal- and lanthanide-mediated construction of carbocycles. Although a great deal has been published on the asymmetric cyclopropanation of styrene, relatively little had been reported for other classes of alkenes. Tae-Jeong Kim of Kyungpook National University has devised (Tetrahedron Lett. 2007, 48, 8014) a Ru catalyst for the cyclopropanation of simple α-olefins such as 1. X. Peter Zhang of the University of South Florida has developed (J. Am.Chem. Soc. 2007, 129, 12074) a Co catalyst for the cyclopropanation of alkenes such as 5 having electron-withdrawing groups. Alexandre Alexakis of the Université de Genève has reported(Angew. Chem. Int. Ed. 2007, 46, 7462) simple monophosphine ligands that enabled enantioselective conjugate addition to prochiral enones, even difficult substrates such as 8. Seunghoon Shin of Hanyang University has found (Organic Lett. 2007, 9, 3539) an Au catalyst that effected the diastereoselective cyclization of 10 to the cyclohexene 11, and Radomir N. Saicic of the University of Belgrade has carried out (Organic Lett. 2007, 9, 5063), via transient enamine formation, the diastereoselective cyclization of 12 to the cyclohexane 13. Alois Fürstner of the Max-Planck- Institut, Mülheim has devised (J. Am. Chem. Soc. 2007, 129, 14836) a Rh catalyst that cyclized the aldehyde 14 to the cycloheptenone 15. Some of the most exciting investigations reported in recent months have been directed toward the direct diastereo- and enantioselective preparation of polycarbocyclic products. Rai-Shung Liu of National Tsing-Hua University has extended (J. Org. Chem. 2007, 72, 567) the intramolecular Pauson-Khand cyclization to the epoxy enyne 16, leading to the 5-5 product 17. Michel R. Gagné of the University of North Carolina has devised (J. Am. Chem. Soc. 2007, 129, 11880) a Pt catalyst that smoothly cyclized the polyene 18 to the 6-6 product 19. Yoshihiro Sato of Hokkaido University and Miwako Mori of the Health Science University of Hokkaido have described (J. Am. Chem. Soc. 2007, 129, 7730) a Ru catalyst for the cyclization of 20 to the 5-6-5 product 21. Each of these processes proceeded with high diastereocontrol.

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