The Synthesis of 5α-Pregnane-3β, 17, α, 21-triol-11, 20-dione (Reichstein's Substance D) and 5α-Pregnane-3β, 11β, 17α, 21-tetrol-20-one (Reichstein's Substance V) …

EM Chamberlin, JM Chemerda

Index: Chamberlin,Chemerda Journal of the American Chemical Society, 1955 , vol. 77, p. 1221,1223

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Citation Number: 16

Abstract

tetrol-20-one (VI) was accomplished by formation of the 20-semicarbazone followed by reduction of the 11-keto group to 11-hydroxyl with sodium borohydride in refluxing methanol. Reversal of the reduced semicarbazone in the usual manner with pyruvic acid in acetic acid gave VI essentially the same as Reichstein's Substance V. 4 Acknowledgment.-The authors are indebted to Messrs. R. Walker and N. Trenner for the infrared spectra, to Mr. Fred ...