An Efficient and Stereoselective Synthesis of Xerulin via Pd-Catalyzed Cross Coupling and Lactonization Featuring (E)-Iodobromoethylene as a Novel Two-Carbon Synthon
Organic Letters1999Vol. 2(1), pp. 65–67
Citations Over TimeTop 14% of 1999 papers
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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