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Synthesis of Alstoscholarisines A–E, Monoterpene Indole Alkaloids with Modulating Effects on Neural Stem Cells

Author:
Mason, Jeremy D., Weinreb, Steven M.
Source:
Journal of organic chemistry 2018 v.83 no.11 pp. 5877-5896
ISSN:
1520-6904
Subject:
adults, aldehydes, chemical reactions, indole alkaloids, moieties, monoterpenoids, neurons, organic chemistry, stem cells, stereoselectivity
Abstract:
A divergent synthetic strategy has been developed for stereoselective total syntheses of alstoscholarisines A–E, monoterpenoid indole alkaloids which are modulators of adult neuronal stem cells. A pivotal step includes an intermolecular Michael addition of an indole-2-acetic acid methyl ester enolate to an α,β-unsaturated N-sulfonyllactam to form the C15, C16 bond of the alkaloids. Other features of the strategy involve a selective partial reduction of an intermediate N-sulfonyllactam followed by cyclization to a bridged aminal system that serves as a key precursor for all five of the alkaloids as well as the use of an allyl group as a masked aldehyde equivalent.
Agid:
6047324