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Total Syntheses of Cyanthiwigins B, F, and G

Author:
John A. Enquist Jr.   Dr. Scott C. Virgil   Prof. Brian M. Stoltz  


Journal:
Chemistry (Weinheim an der Bergstrasse, Germany)


Issue Date:
2011


Abstract(summary):

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. Copyright 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Page:
9957-9969


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