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

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.

SUBMITTER: Seo JH

PROVIDER: S-EPMC2855441 | biostudies-literature | 2010 Apr

REPOSITORIES: biostudies-literature

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

Seo Jae Hong JH Liu Peng P Weinreb Steven M SM

The Journal of organic chemistry 20100401 8

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-al ...[more]

PMID: 20334369

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