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Communication | Special issue | Vol 70, No. 1, 2006, pp.113-118
Published online, 7th November, 2006
DOI: 10.3987/COM-06-S(W)35
Synthetic Studies toward Cribrostatin IV: An Intriguing Epimerization

Collin Chan and Samuel J. Danishefsky*

*Department of Chemistry, MSKCC, Columbia University, Box 106, 1275 York Ave., New York, NY 10021, U.S.A.

Abstract

Surprising effects of remote substituents on the relative rates of vinylogous Pictet-Spengler reaction versus epimerization through a Grigg like progression have been encountered (contrast cyclizations of 3 and 7). Deuterium labeling experiments have been used to clarify mechanisms of epimerization, thereby allowing for the assignment of absolute configuration.