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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
An efficient and stereoselective synthesis of xerulin via Pd-catalyzed cross coupling and lactonization featuring
E Negishi1, A Alimardanov, C Xu
1Herbert C. Brown Laboratories, Purdue University, West Lafayette, Indiana 47907, USA. negishi@purdue.edu
Abstract:
[structure: see text] Xerulin, an inhibitor of cholesterol biosynthesis, has been synthesized from commercially available (E)-1-bromopropene, acetylene, and propynoic acid in five steps (longest linear sequence) in 30% overall yield and >96% stereoselectivity. The preparation of (E)-iodobromoethylene and its use in the Pd-catalyzed cross coupling are two of the novel aspects of the synthesis reported herein.
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