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Total synthesis of (±)-isophellibiline.

ABSTRACT: The total synthesis of (±)-isophellibiline is described. This represents the first synthesis of a member of the nonaromatic homoerythrinan family of alkaloids. The tetracyclic ring system of the natural product was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of an amidodioxin, an intramolecular Heck reaction and a 6?-electrocyclic ring closure of a dienoic acid.

SUBMITTER: Funk RL

PROVIDER: S-EPMC3269829 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Total synthesis of (±)-isophellibiline.

Funk Raymond L RL Belmar Johannes J

Tetrahedron letters 20120101 2

The total synthesis of (±)-isophellibiline is described. This represents the first synthesis of a member of the nonaromatic homoerythrinan family of alkaloids. The tetracyclic ring system of the natural product was quickly assembled by a strategy that features a retrocycloaddition/cycloaddition reaction of an amidodioxin, an intramolecular Heck reaction and a 6π-electrocyclic ring closure of a dienoic acid. ...[more]

PMID: 22308006

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