J. Schmidlin

Über Synthesen in der Aldosteron-Reihe I. Totalsynthese des racemischen Aldosterons

d,l-Aldosterone (XXIV) has been prepared by total synthesis, involving more than 20 new steps, from the tricyclic compound I.

Mikrobiologische Spaltung razemischer Steroide. Synthese vond-Aldosteron

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.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.

Über eine neue Synthese von 18-Hydroxy- und 18-Oxo-progesteron

18-Hydroxyprogesterone (VII) and the corresponding 18-aldehyde (IX), hitherto only accessible with difficulty from natural 18-substituted steroids, have been synthesized starting from progesterone.