An efficient and stereoselective synthesis of xerulin via Pd-catalyzed cross coupling and lactonization featuring (E)-iodobromoethylene as a novel two-carbon synthon
E. Negishi et al., An efficient and stereoselective synthesis of xerulin via Pd-catalyzed cross coupling and lactonization featuring (E)-iodobromoethylene as a novel two-carbon synthon, ORG LETT, 2(1), 2000, pp. 65-67
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Xerulin, an inhibitor of cholesterol biosynthesis, has been synthesized fro
m commercially available (E)-1-bromopropene, acetylene, and propynoic acid
in five steps (longest linear sequence) in 30% overall yield and >96% stere
oselectivity, The preparation of (E)-iodobromoethylene and its use in the P
d-catalyzed cross coupling are two of the novel aspects of the synthesis re
ported herein.