Selective steroid chlorinations directed by attached pyridine ester templates

R Breslow, M Brandl, J Hunger…

Index: Breslow, Ronald; Brandl, Michael; Hunger, Juergen; Adams, Alan D. Journal of the American Chemical Society, 1987 , vol. 109, # 12 p. 3799 - 3801

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Citation Number: 33

Abstract

14-chloro derivative 3. The mixture was analyzed by hydrolysis/dehydrochlorination with KOH to form the known] 9 (1 1) olefin (92% isolated yield) and A14 olefin (3% yield), respectively. With the isonicotinate ester 4, 12 the changed geometry led to 44% recovered starting material, 37% 9 (11) olefin, 14% A14 olefin, and 5% of a product formed by double chlorination.