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A total synthesis of spiruchostatin A
Authors:Takayuki Doi  Yusuke Iijima  A. Ganesan
Affiliation:a Department of Applied Chemistry, Tokyo Institute of Technology, 2-12-1, Ookayama, Meguro, Tokyo 152-8552, Japan
b Institute of Molecular and Cellular Biosciences, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, Tokyo 113-0032, Japan
c Biological Information Research Center (BIRC), National Institute of Advanced Industrial Science and Technology (AIST), Protein Network Team, Low M.W. Chemical Laboratory, AIST Tokyo Waterfront Bio-IT Research Building, 2-42 Aomi, Koto-ku, Tokyo 135-0064, Japan
d School of Chemistry, University of Southampton, Southampton SO17 1BJ, UK
Abstract:We achieved the total synthesis of the histone deacetylase inhibitor spiruchostatin A, as the prelude to the preparation of a combinatorial library of its analogues. Two key reactions were an asymmetric acetate aldol reaction using a Zr-enolate and macrolactonization using the Shiina method.
Keywords:Spiruchostatin   Cyclic depsipeptide   Natural product synthesis   Asymmetric aldol reaction
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