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    【Angew. Chem. Int. Ed.】Structure-Unit-Based Total Synthesis of (-)-Sinulochmodin C

    来源: 日期:2023年11月30日 10:46点击:

    Structure-Unit-Based Total Synthesis of (-)-Sinulochmodin C

    By: Yi-Peng Zhang, Shufei Du, Ying Ma, Weixin Zhan, Wen Chen, Xiaodong Yang, Hongbin Zhang

    Angewandte Chemie - International Edition

    DOI:https://doi.org/10.1002/anie.202315481

    Published:2023-11-27

    Abstract

    Herein we report a structure-unit-based asymmetric total synthesis of sinulochmodin C, a norcembranoid diterpenoid bearing a transannular strained ether bridge beta-keto tetrahydrofuran moiety. Our synthetic route features an intramolecular double Michael addition to construct stereospecifically the [7,6,5,5] tetracyclic skeleton, a vinylogous hydroxylation/oxidation procedure or a stereospecific epoxide opening/oxidation sequence to establish the gamma-keto enone intermediate, a Lewis acid/Bronsted acid mediated transannular oxa-Michael addition to fuse the beta-keto tetrahydrofuran moiety, a Mukaiyama hydration/Pd-C hydrogenation to reverse the C1-configuration of the isopropenyl unit, and a bioinspired transformation of sinulochmodin C into scabrolide A.

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