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Total Synthesis of Isodaphlongamine H: A Possible Biogenetic Conundrum.

par Chattopadhyay, Amit Kumar;Ly, Vu Linh;Jakkepally, Shashidhar ;Berger, Gilles;Hanessian, Stephen
Référence Angewandte Chemie, 55, 7, page (2577-2581)
Publication Publié, 2016-02

Article révisé par les pairs

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Résumé :

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.