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Communication | Special issue | Vol 72, No. 1, 2007, pp.167-174
Published online, 6th February, 2007
DOI: 10.3987/COM-06-S(K)42
Studies toward the Total Synthesis of Grandisine A: Synthesis of 9-epi-Grandisine A

David J. Maloney and Samuel J. Danishefsky*

*Laboratory for Bioorganic Chemistry, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, NY 10021, U.S.A.

Abstract

A concise synthesis of 9-epi-grandisine A is described, which makes use of a Lewis acid-promoted hetero-Diels-Alder reaction to construct the tricyclic skeleton. Attempts to obtain grandisine A through a late-stage controlled epimerization are also discussed.