Biosynthetic studies of marine lipids. 39. 19-Norsterols: the course of C-19 methyl elimination

MH Rabinowitz, C Djerassi

Index: Rabinowitz, Michael H.; Djerassi, Carl Journal of the American Chemical Society, 1992 , vol. 114, # 1 p. 304 - 317

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Citation Number: 20

Abstract

Abstract: The biosynthesis of 19-norstanols in the Mediterranean sponge, Axinella polypoides, was investigated through the use of radiotracer experiments. It was found that the conversion of cholesterol (7) to 19-nor-5a-cholestan-3~-ol (8) involved oxidation at C-3 with the distribution of the abstracted hydride from the 3a-position of dietary cholesterol into all of the 19-norstanols of the native mixture. Furthermore, while the efficiency of ...