Total syntheses of the monoterpene indole alkaloids (±)- alstilobanine A and e and (±)-angustilodine

Yiqing Feng, Max M. Majireck, Steven M. Weinreb

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23 Scopus citations

Abstract

A synthetic strategy has been developed culminating in stereoselective total syntheses of the small class of unusual monoterpenoid indole alkaloids exemplified by alstilobanines A (3) and E (2) and angustilodine (1). A pivotal step includes a novel intermolecular Michael-type addition of an indole ester dianion to a piperidine-derived nitrosoalkene to form the C15, C16 bond of the alkaloids. In addition, an application of the Romo protocol for effecting a stereoselective intramolecular nucleophile-assisted aldol-lactonization was employed, leading to a β-lactone incorporating the requisite cis-fused 2-azadecalin moiety and also setting the C15, C19, C20 relative stereochemistry of the metabolites. It was then possible to stereoselectively effect an aldolization of a dianion derived from this indole ester β-lactone intermediate with formaldehyde to introduce the requisite C16 hydroxymethyl group. Further manipulations of the system ultimately led to the three alkaloids in racemic form.

Original languageEnglish (US)
Pages (from-to)7-24
Number of pages18
JournalJournal of Organic Chemistry
Volume79
Issue number1
DOIs
StatePublished - Jan 3 2014

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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