Synthesis of the cis-fused hexahydroxanthene system via cationic cascade cyclization

Jeffrey D. Neighbors, Joseph J. Topczewski, Dale C. Swenson, David F. Wiemer

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The cis-fused hexahydroxanthene system can be obtained through a cascade cyclization initiated by Lewis acid-mediated epoxide opening and terminated by reaction with a MOM-protected phenol. Only a single diastereomer of the product was obtained with stereochemistry verified by diffraction analysis. This demonstrates the viability of this approach to natural products containing the cis-fused hexahydroxanthene skeleton, and supports preparation of more complex targets through a similar strategy.

Original languageEnglish (US)
Pages (from-to)3881-3884
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number27
DOIs
StatePublished - Jul 8 2009

Bibliographical note

Funding Information:
Financial support in the form of a Shriner Fellowship (to J.J.T.) and from the Roy J. Carver Charitable Trust is gratefully acknowledged.

Copyright:
Copyright 2009 Elsevier B.V., All rights reserved.

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