132971-61-0Relevant articles and documents
First synthesis of Xerulin, an inhibitor of the biosynthesis of cholesterol
Siegel, Konrad,Brückner, Reinhard
, p. 1227 - 1230 (1999)
Starting from L-ascorbic acid, crotonaldehyde, (trimethylsilyl)acetylene and the stannylated alcohol 15, the title compound 4 was synthesized for the first time. L-Ascorbic acid was elaborated into phosphonium bromide 19 with a high degree of Z-stereoselectivity while the other starting materials were combined for obtaining the unsaturated aldehyde 5. A Wittig reaction between this aldehyde and the ylide derived from bromide 19 provided xerulin (4) along with a mixture of isomers which was readily separable.
An efficient and stereoselective synthesis of xerulin via Pd-catalyzed cross coupling and lactonization featuring (E)-lodobromoethylene as a novel two-carbon synthon.
Negishi,Alimardanov,Xu
, p. 65 - 67 (2000)
[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.
