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

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

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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

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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