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Mikrobiologische Spaltung razemischer Steroide. Synthese vond-Aldosteron

Research paper by E. Vischer, J. Schmidlin, A. Wettstein

Indexed on: 01 Feb '56Published on: 01 Feb '56Published in: Cellular and Molecular Life Sciences



Abstract

A racemic intermediate in the total synthesis ofd, l-aldosterone, thed, l-20-oxo-pregnene derivative I, was converted by incubation with a mold hydroxylating in the 21-position into thed-20-oxo-21-hydroxy-pregnene derivative II, whereas thel-antipode of the starting material remained unchanged. This stereospecific microbiological reaction, comprising a separation of racemic modifications, represents the last remaining step in the synthesis of naturald-aldosterone.Other microbiological conversions of racemic steroids, dehydrogenation and hydrogenation, were also shown to proceed only with thed-enantiomer, leaving thel-form of thed, l-substrate intact.The advantages of this new microbiological method for the resolution of racemic modifications during the total synthesis of steroids are discussed.