國家衛生研究院 NHRI:Item 3990099045/11496
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    题名: Biomimetic Syntheses of (±)‐Isopalhinine A, (±)‐Palhinine A, and (±)‐Palhinine D
    作者: Chen, CM;Shiao, HY;Uang, BJ;Hsieh, HP
    贡献者: Institute of Biotechnology and Pharmaceutical Research
    摘要: The first total synthesis of isopalhinine A, as well as unified syntheses of palhinine A and palhinine D, have been successfully accomplished by way of a biomimetic strategy that proceeds through a bio-inspired 5/6/6/9 tetracyclic intermediate, which mimics the amino ketone form of palhinine D. An early-stage direct SN2 cyclization to construct the nine-membered azonane ring minimized the transannular strain which would otherwise be increased by the twisted nature of the isotwistane skeleton; then, a diastereoselective Diels-Alder reaction of a masked ortho-benzoquinone using the nine-membered ring as a steric shielding group furnished a functionalized 6/6/9 tricyclic skeleton and established the desired stereochemistry at the C3, C7, C12, and C15 positions in one step. A thiol-mediated acyl radical cyclization gave the bio-inspired intermediate bearing three differentiated oxygen-containing functional groups, from which all three total syntheses could be completed in either two or three additional steps.
    日期: 2018-11
    關聯: Angewandte Chemie. 2018 Nov;57(47):15572-15576.
    Link to: http://dx.doi.org/10.1002/anie.201809130
    JIF/Ranking 2023: http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=NHRI&SrcApp=NHRI_IR&KeyISSN=1433-7851&DestApp=IC2JCR
    Cited Times(WOS): https://www.webofscience.com/wos/woscc/full-record/WOS:000453344500049
    Cited Times(Scopus): https://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85055931709
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