Evolution of a strategy for total synthesis of the marine fungal alkaloid (±)-communesin F

Jae Hong Seo, Peng Liu, Steven M. Weinreb

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36 Scopus citations

Abstract

A new synthetic strategy for construction of the heptacyclic marine fungal alkaloid (±)-communesin F has been devised. Key reactions include an intramolecular Heck cyclization of a tetrasubstituted alkene to generate a tetracyclic enamide bearing one of the quaternary carbon centers (C7) of the alkaloid, an intramolecular reductive cyclization of an N-Boc aniline onto the oxindole moiety to form a pentacyclic framework containing the southern aminal, a stereoselective N-Boc-lactam enolate C-allylation to introduce the second quaternary carbon center (C8), and an azide reduction/N-Boc-lactam-opening cascade leading to the northern aminal.

Original languageEnglish (US)
Pages (from-to)2667-2680
Number of pages14
JournalJournal of Organic Chemistry
Volume75
Issue number8
DOIs
StatePublished - Apr 16 2010

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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