Total Synthesis of Isodaphlongamine H: A Possible Biogenetic Conundrum

Angewandte Chemie
Amit Kumar ChattopadhyayStephen Hanessian

Abstract

Herein we describe the first synthetic efforts toward the total synthesis of isodaphlongamine H, a calyciphylline B-type alkaloid. The strategy employs a chemoenzymatic process for the preparation of a functionalized cyclopentanol with a quaternary center. This molecule is elaborated to form an enantiopure 1-aza-perhydrocyclopentalene core, representing rings A and E of all calyciphylline B-type alkaloids. Further transformations involve the formation of a cyclic enaminone, 1,4-conjugate addition with a cyclopentenyl subunit, and intramolecular aldol cyclization to achieve a pentacyclic intermediate, ultimately forming isodaphlongamine H in a total of 24 steps from the commercially available compound 2-carbethoxycyclopentanone. Isodaphlongamine H exhibits promising inhibitory activity against a panel of human cancer cell lines.

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Citations

Feb 16, 2016·The Journal of Organic Chemistry·Amit Kumar ChattopadhyayStephen Hanessian
Jun 3, 2016·The Journal of Organic Chemistry·Amit Kumar ChattopadhyayStephen Hanessian
Feb 17, 2017·Chemical Reviews·Amit Kumar Chattopadhyay, Stephen Hanessian
Mar 16, 2017·Organic Letters·Jian Long LiJun Yang
Jul 1, 2017·Organic Letters·Patrick Boissarie, Guillaume Bélanger
May 16, 2018·Chemical Communications : Chem Comm·Yuanyou QiuShuanhu Gao
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Apr 9, 2019·Angewandte Chemie·Yuye ChenJing Xu
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