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

Jeremy D. Mason, Steven M. Weinreb

Research output: Contribution to journalArticle

9 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)5877-5896
Number of pages20
JournalJournal of Organic Chemistry
Volume83
Issue number11
DOIs
StatePublished - Jun 1 2018

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Indole Alkaloids
Monoterpenes
Stem cells
Alkaloids
Secologanin Tryptamine Alkaloids
Cyclization
Aldehydes
Modulators
indole
methyl acetate

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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Synthesis of Alstoscholarisines A-E, Monoterpene Indole Alkaloids with Modulating Effects on Neural Stem Cells. / Mason, Jeremy D.; Weinreb, Steven M.

In: Journal of Organic Chemistry, Vol. 83, No. 11, 01.06.2018, p. 5877-5896.

Research output: Contribution to journalArticle

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