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Stereodivergent Synthesis of (+)- and (−)-Isolineatin
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    Stereodivergent Synthesis of (+)- and (−)-Isolineatin
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    Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2013, 78, 9, 4483–4489
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    https://doi.org/10.1021/jo400487y
    Published April 12, 2013
    Copyright © 2013 American Chemical Society

    Abstract

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    A stereodivergent approach to (+)- and (−)-isolineatin using (S)-4-methyl-5-pivaloyloxymethyl-2(5H)-furanone as the single source of asymmetry by exploiting the inherent chirality at the C-5 stereocenter is described.

    Copyright © 2013 American Chemical Society

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    Supporting Information

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    General experimental procedures, 1H and 13C NMR spectra of all new compounds, and 2-D NMR spectra for compounds 8, 9, 12, 16, 20, and 28. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 8 publications.

    1. Saner Poplata, Andreas Tröster, You-Quan Zou, and Thorsten Bach . Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions. Chemical Reviews 2016, 116 (17) , 9748-9815. https://doi.org/10.1021/acs.chemrev.5b00723
    2. Guillaume Lejeune, Josep Font, Teodor Parella, Ramon Alibés, and Marta Figueredo . Intramolecular Photoreactions of (5S)-5-Oxymethyl-2(5H)-furanones as a Tool for the Stereoselective Generation of Diverse Polycyclic Scaffolds. The Journal of Organic Chemistry 2015, 80 (19) , 9437-9445. https://doi.org/10.1021/acs.joc.5b01354
    3. Simen Antonsen, Runa B. Østby, Yngve Stenstrøm. Naturally Occurring Cyclobutanes: Their Biological Significance and Synthesis. 2018, 1-40. https://doi.org/10.1016/B978-0-444-64057-4.00001-6
    4. Maxime Fréneau, Pascal de Sainte‐Claire, Manabu Abe, Norbert Hoffmann. The structure of electronically excited α,β‐unsaturated lactones. Journal of Physical Organic Chemistry 2016, 29 (12) , 718-724. https://doi.org/10.1002/poc.3560
    5. Ramon Flores, Josep Font, Ramon Alibés, Marta Figueredo. A Study on the Photoreaction of 2(5 H )‐Furanones with Substituted Acetylenes: Evidence for a Mechanistic Reformulation. Chemistry – A European Journal 2016, 22 (11) , 3835-3845. https://doi.org/10.1002/chem.201503888
    6. Zhong-Yi Mao, Hui Geng, Tian-Tian Zhang, Yuan-Ping Ruan, Jian-Liang Ye, Pei-Qiang Huang. Stereodivergent and enantioselective total syntheses of isochaetominines A–C and four pairs of isochaetominine C enantiomers: a six-step approach. Organic Chemistry Frontiers 2016, 3 (1) , 24-37. https://doi.org/10.1039/C5QO00298B
    7. Rong Jun He, Bing Chun Zhu, Yu Guang Wang. Lewis base‐catalyzed electrophilic lactonization of selenyl bromide resin and facile solid‐phase synthesis of furan‐2(5 H )‐one derivatives. Applied Organometallic Chemistry 2014, 28 (7) , 523-528. https://doi.org/10.1002/aoc.3157
    8. Jing Pei Huo, Guo Hua Deng, Wei Wu, Jin Feng Xiong, Ming Li Zhong, Zhao Yang Wang. Electrophoretic Deposition Polymerization of Diacetylenes with Tunable Structure. Macromolecular Rapid Communications 2013, 34 (22) , 1779-1784. https://doi.org/10.1002/marc.201300637

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2013, 78, 9, 4483–4489
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo400487y
    Published April 12, 2013
    Copyright © 2013 American Chemical Society

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