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Journal articles on the topic 'Asymmetric synthesis. Lactones'

Author: Grafiati

Published: 4 June 2021

Last updated: 8 February 2022

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1

Mondon, M., and J. Gesson. "Asymmetric Synthesis of Styryl-Lactones." Current Organic Synthesis 3, no. 1 (2006): 41–75. http://dx.doi.org/10.2174/157017906775473966.

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2

Shimotori, Yasutaka, Kazuki Sekine та Tetsuo Miyakoshi. "Asymmetric synthesis ofδ-lactones with lipase catalyst". Flavour and Fragrance Journal 22, № 6 (2007): 531–39. http://dx.doi.org/10.1002/ffj.1836.

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3

Wong, Leon S. M., Kathleen A. Turner, Jonathan M. White, Andrew B. Holmes, and John H. Ryan. "Asymmetric Synthesis of a Hydroxylated Nine-membered Lactone from Tartaric Acid using the Claisen Rearrangement." Australian Journal of Chemistry 63, no. 3 (2010): 529. http://dx.doi.org/10.1071/ch09637.

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The synthesis of a hydroxylated vinyl-appended lactone, in five synthetic steps from tartaric acid, is reported. The C2-symmetrical bis-vinyl diol 12 was converted into the ketene acetal 14 via methylenation of the cyclic carbonate 13 or thermal elimination of benzeneselenenic acid from the selenoxide 17. In both cases, the in situ generated ketene acetal 14 underwent spontaneous Claisen rearrangement to give the nine-membered lactone (+)-15. Lactones of this type are potentially advanced precursors to simplified eleutherobin analogues or other medium-ring lactone natural products.

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4

Li, Yanjun, та Taeko Izumi. "Asymmetric Synthesis of Chiral δ-lactones using BINAP-ruthenium(II) Complexes Hydrogenation Catalysts". Journal of Chemical Research 2002, № 11 (2002): 567–69. http://dx.doi.org/10.3184/030823402103170790.

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Asymmetric hydrogenation of keto-acids was accomplished by catalytic amounts of BINAP-ruthenium complexes to afford the corresponding δ-lactones in high yields. The optical purity of the synthesised δ-lactones was determined by chiralcel (OD) in the 9–56% range.

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5

Yang, Jiaxin, Xiuxiu Li, Cai You та ін. "Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds". Organic & Biomolecular Chemistry 18, № 5 (2020): 856–59. http://dx.doi.org/10.1039/c9ob02536g.

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6

Ray Choudhury, Abhijnan, and Santanu Mukherjee. "Deconjugated butenolide: a versatile building block for asymmetric catalysis." Chemical Society Reviews 49, no. 18 (2020): 6755–88. http://dx.doi.org/10.1039/c9cs00346k.

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Deconjugated butenolides have emerged as a popular synthon for the enantioselective synthesis of γ-lactones. This review provides a comprehensive overview on the catalytic asymmetric reactions of deconjugated butenolides reported till date.

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7

Nagao, Yoshimitsu, Toshiaki Tohjo, Masahito Ochiai та Motoo Shiro. "Expeditious Asymmetric Synthesis of Optically Pure δ-Lactones Bearing Consecutive Three Asymmetric Centers". Chemistry Letters 21, № 2 (1992): 335–38. http://dx.doi.org/10.1246/cl.1992.335.

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8

Marco, J. Alberto, and Miguel Carda. "Stereoselective Synthesis of Five Biologically Active, Naturally Occurring Medium and Large Ring Lactones." Natural Product Communications 6, no. 4 (2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600411.

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Stereoselective syntheses of five naturally occurring, pharmacologically active medium and large ring lactones are described. Key synthetic methods used were, depending on the cases, olefin metatheses, asymmetric allylations and C-glycosidations.

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9

Gaikwad, Ravindra D., Monica D. Rane та Sujata V. Bhat. "Asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones". Tetrahedron: Asymmetry 28, № 1 (2017): 181–85. http://dx.doi.org/10.1016/j.tetasy.2016.12.006.

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10

Peed, Jennifer, Ignacio Periñán Domínguez, Iwan R. Davies та ін. "Asymmetric Synthesis of Chiral δ-Lactones Containing Multiple Contiguous Stereocenters". Organic Letters 13, № 14 (2011): 3592–95. http://dx.doi.org/10.1021/ol2012023.

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11

Campagne, J. M., B. Bazán-Tejeda, G. Bluet та G. Broustal. "Cu-Catalyzed Asymmetric Synthesis of α,β-Unsaturated δ-Lactones". Synfacts 2007, № 1 (2007): 0073. http://dx.doi.org/10.1055/s-2006-955732.

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12

Xiong, Zhichao, Jiangyan Tian, Peng Xue, Xumu Zhang та Hui Lv. "Enantioselective synthesis of chiral multicyclic γ-lactones via dynamic kinetic resolution of racemic γ-keto carboxylic acids". Organic Chemistry Frontiers 7, № 1 (2020): 104–8. http://dx.doi.org/10.1039/c9qo01047e.

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13

Ramachandran, P. Veeraraghavan, M. Venkat Ram Reddy, and Herbert C. Brown. "Tandem allylboration-ring-closing metathesis reactions for the preparation of biologically active molecules." Pure and Applied Chemistry 75, no. 9 (2003): 1263–75. http://dx.doi.org/10.1351/pac200375091263.

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The development of asymmetric synthesis during the past two decades aided organic chemists considerably in the synthesis of complex natural products. Organoborane chemistry continues to play an important role in asymmetric synthesis. One of the important reactions that has become very common in the arsenal of synthetic chemists is allylboration and related reactions. Another important reaction that has recently attained enormous importance in organic chemistry is the ring-closing metathesis (RCM) reaction. Indeed, a combination of allylboration and RCM reactions provides an excellent route to

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14

Helmchen, G., Martin Ernst, and G. Paradies. "Application of allylic substitutions in natural products synthesis." Pure and Applied Chemistry 76, no. 3 (2004): 495–505. http://dx.doi.org/10.1351/pac200476030495.

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Synthesis routes are described, allowing all known jasmonoids as well as their enantiomers to be synthesized in enantiomerically and diastereomerically pure form. The routes are based on a set of closely related lactones containing an electrophilic allylic moiety, which are accessible via asymmetric Pd-catalyzed allylic alkylation. Regio- and diastereoselective SN2'-anti-reactions of the electrophilic lactones with organocopper compounds furnished 2,3-cis-disubstituted cyclopentenones, which were further transformed into the target compounds, i.e., 12-oxophytodienoic acid (12-OPDA) in excellen

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15

Zhou, Wei-Shan, and Zhi-Cai Yang. "Asymmetric Total Synthesis of Antitumor Styryl Lactones and Related Natural Products." HETEROCYCLES 45, no. 2 (1997): 367. http://dx.doi.org/10.3987/rev-96-487.

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16

Chen, Shi, Ahmad A. Ibrahim, Nicholas J. Peraino та ін. "Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations". Journal of Organic Chemistry 81, № 17 (2016): 7824–37. http://dx.doi.org/10.1021/acs.joc.6b01481.

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17

Paju, Anne, Marit Laos, Artur Jõgi та ін. "Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones". Tetrahedron Letters 47, № 26 (2006): 4491–93. http://dx.doi.org/10.1016/j.tetlet.2006.04.013.

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18

NAGAO, Y., T. TOHJO, M. OCHIAI та M. SHIRO. "ChemInform Abstract: Expeditious Asymmetric Synthesis of Optically Pure δ-Lactones Bearing Consecutive Three Asymmetric Centers." ChemInform 23, № 50 (2010): no. http://dx.doi.org/10.1002/chin.199250076.

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19

Bringmann, Gerhard, Robert-Michael Pfeifer, Christian Rummey, Thomas Pabst, Dirk Leusser, and Dietmar Stalke. "Structural Investigation of a Configurationally Stable Seven-Membered Bridged Biaryl of Relevance for Atroposelective Biaryl Syntheses*." Zeitschrift für Naturforschung B 58, no. 2-3 (2003): 231–36. http://dx.doi.org/10.1515/znb-2003-2-305.

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The atroposelective ring opening of lactone-bridged biaryl systems is the key step in the total synthesis of a series of axially chiral biaryl natural products and useful reagents or catalysts for asymmetric synthesis. For a more in-depth understanding of the mechanism and stereochemical course of this remarkable cleavage reaction, a seven-membered ether analog of such useful biaryl lactones has been investigated structurally, both experimentally, by X-ray diffraction analysis, and by ab initio calculations (B3LYP/6-31G*). In a nearly perfect agreement, both methods show that these seven-membe

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20

Kernen, Philippe, and Pierre Vogel. "Total asymmetric synthesis of polypropionate fragments and doubly branched heptono-1,4-lactones." Tetrahedron Letters 34, no. 15 (1993): 2473–76. http://dx.doi.org/10.1016/s0040-4039(00)60444-6.

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21

KAWAKAMI, Yukio, Jun HIRATAKE, Yukio YAMAMOTO, and Jun''ichi ODA. "An asymmetric synthesis of lactones from cyclic acid anhydrides with chiral binaphthyldiamines." Agricultural and Biological Chemistry 50, no. 3 (1986): 693–98. http://dx.doi.org/10.1271/bbb1961.50.693.

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22

Liu, Qiang, Sun Li, Xiang-Yu Chen, Kari Rissanen та Dieter Enders. "Asymmetric Synthesis of Spiro-oxindole-ε-lactones through N-Heterocyclic Carbene Catalysis". Organic Letters 20, № 12 (2018): 3622–26. http://dx.doi.org/10.1021/acs.orglett.8b01400.

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23

Chen, Shi, Mukulesh Mondal, Ahmad A. Ibrahim, Kraig A. Wheeler та Nessan J. Kerrigan. "Phosphine-Catalyzed Asymmetric Synthesis of β-Lactones from Disubstituted Ketenes and Aldehydes". Journal of Organic Chemistry 79, № 11 (2014): 4920–29. http://dx.doi.org/10.1021/jo500486e.

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24

Mondal, Mukulesh, Ahmad A. Ibrahim, Kraig A. Wheeler та Nessan J. Kerrigan. "Phosphine-Catalyzed Asymmetric Synthesis of β-Lactones from Arylketoketenes and Aromatic Aldehydes". Organic Letters 12, № 8 (2010): 1664–67. http://dx.doi.org/10.1021/ol100075m.

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25

Peed, Jennifer, Ignacio Perinan Dominguez, Iwan R. Davies та ін. "ChemInform Abstract: Asymmetric Synthesis of Chiral δ-Lactones Containing Multiple Contiguous Stereocenters." ChemInform 42, № 48 (2011): no. http://dx.doi.org/10.1002/chin.201148140.

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26

Kawakami, Yukio, Jun Hiratake, Yukio Yamamoto, and Jun’ichi Oda. "An Asymmetric Synthesis of Lactones from Cyclic Acid Anhydrides with Chiral Binaphthyldiamines." Agricultural and Biological Chemistry 50, no. 3 (1986): 693–98. http://dx.doi.org/10.1080/00021369.1986.10867431.

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27

Dong, Chune, and Howard Alper. "Catalytic Asymmetric Cyclocarbonylation ofo-Isopropenylphenols: Enantioselective Synthesis of Six-Membered Ring Lactones." Journal of Organic Chemistry 69, no. 15 (2004): 5011–14. http://dx.doi.org/10.1021/jo040109f.

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28

Hao, Xiaoyu, Xiaohua Liu, Wei Li та ін. "Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones". Organic Letters 16, № 1 (2013): 134–37. http://dx.doi.org/10.1021/ol4031217.

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29

Doda, Sai Reddy, Avula Raghavendar, Sharath Babu Haridasyam, Chandra Shekar Putta, Bhattu Kanakadurga rao, and Sudhakar Kadari. "Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol." Heterocyclic Communications 25, no. 1 (2019): 78–84. http://dx.doi.org/10.1515/hc-2019-0015.

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AbstractAn efficient, short and, a convenient asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol (2) and zeaenol (1) have been achieved in 7 and 9 linear steps with the high overall yield of 32% and 21% respectively, from the known intermediate 13. Mitsunobu inversion, De Brabander’s protocol for macrolactonisation, Heck cross-coupling, diastereoselective alkyne aldehyde coupling and Ohira–Bestmann alkynylation are the key reactions.

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30

Trova, Michael P., Allan Wissner, Wellington T. Casscles та Grace C. Hsu. "Asymmetric synthesis of cis- and trans-γ-lactones useful in HIV-1 protease inhibitor synthesis". Bioorganic & Medicinal Chemistry Letters 4, № 7 (1994): 903–6. http://dx.doi.org/10.1016/s0960-894x(01)80260-2.

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31

Curran, Dennis P., and Sung-Bo Ko. "Synthesis of Optically Active .alpha.-Hydroxy Lactones by Sharpless Asymmetric Dihydroxylations of Ketene Acetals, Enol Ethers, and Ene Lactones." Journal of Organic Chemistry 59, no. 21 (1994): 6139–41. http://dx.doi.org/10.1021/jo00100a005.

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32

Hu, Bin, та Li Deng. "Direct Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Esters/Lactones via Umpolung Strategy". Journal of Organic Chemistry 84, № 2 (2018): 994–1005. http://dx.doi.org/10.1021/acs.joc.8b02893.

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33

Peraino, Nicholas J., Han-Jen Ho, Mukulesh Mondal та Nessan J. Kerrigan. "Asymmetric synthesis of γ-lactones through reaction of sulfoxonium ylides, aldehydes, and ketenes". Tetrahedron Letters 55, № 30 (2014): 4260–63. http://dx.doi.org/10.1016/j.tetlet.2014.05.130.

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34

YANG, Z. C., and W. S. ZHOU. "ChemInform Abstract: Asymmetric Total Synthesis of Antitumor Styryl Lactones and Related Natural Products." ChemInform 28, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199733346.

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35

Kull, Thomas, та René Peters. "Contact Ion Pair Directed Lewis Acid Catalysis: Asymmetric Synthesis oftrans‐Configured β‐Lactones". Angewandte Chemie International Edition 47, № 29 (2008): 5461–64. http://dx.doi.org/10.1002/anie.200801143.

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36

Raffaelli, Barbara, Kristiina Wähälä, and Tapio Hase. "Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones." Org. Biomol. Chem. 4, no. 2 (2006): 331–41. http://dx.doi.org/10.1039/b513303c.

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37

Zemribo, Ronald, та Daniel Romo. "Highly diastereoselective [2+2] cycloadditions via chelation control: Asymmetric synthesis of β-lactones". Tetrahedron Letters 36, № 24 (1995): 4159–62. http://dx.doi.org/10.1016/0040-4039(95)00716-p.

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38

Bourboula, Asimina, Dimitris Limnios, Maroula G. Kokotou, Olga G. Mountanea та George Kokotos. "Enantioselective Organocatalysis-Based Synthesis of 3-Hydroxy Fatty Acids and Fatty γ-Lactones". Molecules 24, № 11 (2019): 2081. http://dx.doi.org/10.3390/molecules24112081.

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3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesiu

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39

Hao, Xiaoyu, Xiaohua Liu, Wei Li та ін. "ChemInform Abstract: Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones." ChemInform 45, № 24 (2014): no. http://dx.doi.org/10.1002/chin.201424031.

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40

Enders, Dieter, Juan Vázquez та Gerhard Raabe. "Formaldehyde SAMP-Hydrazone as a Neutral Formyl Anion Equivalent: Asymmetric Synthesis of Substituted β-Formyl δ-Lactones and Furofuran Lactones". European Journal of Organic Chemistry 2000, № 6 (2000): 893–901. http://dx.doi.org/10.1002/(sici)1099-0690(200003)2000:6<893::aid-ejoc893>3.0.co;2-u.

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41

Cai, Quan, Xu-Ge Si, and Zhi-Mao Zhang. "Asymmetric Inverse-Electron-Demand Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis." Synlett 32, no. 10 (2021): 947–54. http://dx.doi.org/10.1055/a-1371-4391.

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AbstractDiels–Alder reactions of 2-pyrones with alkenes can provide highly functionalized [2,2,2]-bicyclic lactones under mild reaction conditions. Synthetic utilizations of these reactions have been well demonstrated in natural-product synthesis. Although several catalytic asymmetric strategies have been realized, current research in this area is still largely underdeveloped. Recent advances in enantioselective inverse-electron-demand Diels–Alder reactions with Lewis acid catalysis are reviewed.1 Introduction2 State of the Art of Enantioselective Diels–Alder Reactions of 2-Pyrones by Lewis Ac

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42

Buttero, Paola, and Deborah Montrasio. "Tricarbonyl(h6-Arene)Chromium(0) Complexes as Chiral Auxiliaries: Asymmetric Synthesis of b-Lactones." Molecules 6, no. 12 (2001): 13–20. http://dx.doi.org/10.3390/60100013.

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43

Enders, Dieter, та Mareile Haas. "Asymmetric Synthesis of 4,5-Disubstituted 3-Hydroxy δ-Lactones: Prelactone B and Prelactone V". Synlett, № 14 (2003): 2182–84. http://dx.doi.org/10.1055/s-2003-42060.

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44

Cortez, Guillermo S., Reginald L. Tennyson та Daniel Romo. "Intramolecular, Nucleophile-Catalyzed Aldol-Lactonization (NCAL) Reactions: Catalytic, Asymmetric Synthesis of Bicyclic β-Lactones". Journal of the American Chemical Society 123, № 32 (2001): 7945–46. http://dx.doi.org/10.1021/ja016134+.

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45

Chen, Shi, Mukulesh Mondal, Ahmad A. Ibrahim, Kraig A. Wheeler та Nessan J. Kerrigan. "ChemInform Abstract: Phosphine-Catalyzed Asymmetric Synthesis of β-Lactones from Disubstituted Ketenes and Aldehydes." ChemInform 45, № 48 (2014): no. http://dx.doi.org/10.1002/chin.201448106.

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46

Wang, Yang, Lingling Deng, Jie Zhou, et al. "Synthesis of Chiral Sulfonyl Lactones via Copper-Catalyzed Asymmetric Radical Reaction of DABCO⋅(SO2 )." Advanced Synthesis & Catalysis 360, no. 6 (2018): 1060–65. http://dx.doi.org/10.1002/adsc.201701532.

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47

Mondal, Mukulesh, Ahmad A. Ibrahim, Kraig A. Wheeler та Nessan J. Kerrigan. "ChemInform Abstract: Phosphine-Catalyzed Asymmetric Synthesis of β-Lactones from Arylketoketenes and Aromatic Aldehydes." ChemInform 41, № 35 (2010): no. http://dx.doi.org/10.1002/chin.201035108.

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48

Davies, Stephen G., Rebecca L. Nicholson, and Andrew D. Smith. "Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones." Organic & Biomolecular Chemistry 2, no. 22 (2004): 3385. http://dx.doi.org/10.1039/b411724g.

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49

Marino, J. P., та Roberto Fernández de la Pradilla. "Stereospecific synthesis of γ-butyrolactones from acyclic vinyl sulfoxides: an asymmetric synthesis of optically pure oak lactones". Tetrahedron Letters 26, № 44 (1985): 5381–84. http://dx.doi.org/10.1016/s0040-4039(00)98213-3.

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50

TROVA, M. P., A. WISSNER, W. T. JUN CASSCLES та G. C. HSU. "ChemInform Abstract: Asymmetric Synthesis of cis- and trans-γ-Lactones Useful in HIV- 1 Protease Inhibitor Synthesis." ChemInform 25, № 40 (2010): no. http://dx.doi.org/10.1002/chin.199440208.

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