Steroids 2010-03-01

Deacylation reactions of 20-acetyl dinorcholanic lactones and 20,23-diacetyl furost-22-enes.

Ma Guadalupe Hernández-Linares, Jesús Sandoval-Ramírez, Socorro Meza-Reyes, Sara Montiel-Smith, María A Fernández-Herrera, Sylvain Bernès

Index: Steroids 75(3) , 240-4, (2010)

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Abstract

We report the deacylation of (20R)-20-acetyl-23,24-dinorcholanic lactones by hydrazine hydrate, under microwave irradiation in high yields. The elimination of the 20-acetyl group proceeded with retention of configuration which contrast with other proved deacylation methods that yield a mixture of diastereoisomers. In this way, unnatural (20R)-23,24-dinorcholanic lactones can be produced rapidly on a large scale. Both (20R)- and (20S)-lactones were prepared starting from diosgenin, hecogenin and sarsasapogenin, in 72-80% overall yields.Copyright 2009 Elsevier Inc. All rights reserved.