Divergent Entry to Gelsedine-Type Alkaloids: Total Syntheses of (-)-Gelsedilam, (-)-Gelsenicine, (-)-Gelsedine, and (-)-Gelsemoxonine

Journal of the American Chemical Society
Pingluan WangDawei Ma

Abstract

The gelsedine-type alkaloids possess a common oxabicyclo[3.2.2]nonane core and spiro- N-methoxyindolinone moiety along with a diversely functionalized heterocycle embedded in the compact framework. Herein we disclose a divergent entry to gelsedine-type alkaloids that hinges on rapid assembly of the common core by the orchestrated application of an asymmetric Michael addition, a tandem oxidation/aldol cyclization, and a pinacol rearrangement and generation of the structural diversity via a late-stage heterocyclization. The power of this strategy has been demonstrated through very short total syntheses of four gelsedine-type alkaloids: gelsedilam, gelsenicine, gelsedine, and gelsemoxonine.

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Citations

Jan 16, 2021·Accounts of Chemical Research·Yang Gao, Dawei Ma
Mar 13, 2019·ACS Chemical Biology·Florian MayerthalerAlbert A Antolin
Jan 7, 2020·The Journal of Organic Chemistry·Zaki K PhelanDaniel R Griffith
Apr 9, 2019·Journal of the American Chemical Society·Zhen ZhangYun Li

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