The Journal of Organic Chemistry

Enantioselective rhodium-mediated synthesis of (-)-PGE2 methyl ester

DF Taber, RS Hoerrner

文献索引：Taber, Douglass F.; Hoerrner, R. Scott Journal of Organic Chemistry, 1992 , vol. 57, # 2 p. 441 - 447

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被引用次数: 62

摘要

Intramolecular Rh (I1) carboxylate catalyzed cyclization of an a-diazo@-methylene ketone to form a fused cyclopropane is shown to compete efficiently with 8-hydride elimination, so long as a catalyst derived from an electron-donating carboxylate is used. Cyclization of diazoketone 3 gives 2, which on opening with thiophenol followed by oxidative rearrangement gives PGE, methyl ester 1. Prostaglandins having the 8-8 configuration, ...