The Journal of Organic Chemistry

Enantioselective ring construction: synthesis of (+)-estrone methyl ether

DF Taber, K Raman, MD Gaul

Index: Taber, Douglass F.; Raman, Krishna; Gaul, Micheal D. Journal of Organic Chemistry, 1987 ,  vol. 52,  # 1  p. 28 - 34

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Citation Number: 75

Abstract

A general method for the construction of functionalized cyclopentane derivatives 10 of high optical purity, via diastereoselective intramolecular CH insertion, is described. A methylation- retro Dieckmann dianion alkylation procedure on 10b (R= vinyl) gives 12. Decarbomethoxylation of 12 followed by thermolysis yields (+)-estrone methyl ether 1 having 91% ee.