Total Syntheses of Cyanthiwigins B, F, and G

John A. Enquist, Scott C. Virgil, Brian M. Stoltz

Research output: Contribution to journalArticlepeer-review

38 Scopus citations

Abstract

A concise and versatile approach toward the preparation of the cyanthiwigin family of cyathane natural products is described. By leveraging a unique double asymmetric catalytic alkylation procedure it is possible to quickly establish two of the most critical stereocenters of the cyanthiwigin framework with high levels of selectivity and expediency. The synthetic route additionally employs both a tandem ring-closing cross-metathesis reaction, and an aldehyde-olefin radical cyclization process, in order to rapidly arrive at the tricyclic cyathane core of the cyanthiwigin molecules. From this unifying intermediate, the preparations of cyanthiwigins B, F, and G are attained swiftly and without the need for protecting groups.
Original languageEnglish (US)
Pages (from-to)9957-9969
Number of pages13
JournalChemistry - A European Journal
Volume17
Issue number36
DOIs
StatePublished - Jul 18 2011
Externally publishedYes

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