Abstract

IGLESIAS-ARTEAGA, Martín A. et al. A Convenient Procedure for the Synthesis of 3β-Hydroxy-6-oxo-5α-steroids: Application to the Synthesis of Laxogenin. J. Mex. Chem. Soc [online]. 2005, vol.49, n.2, pp.134-142. ISSN 1870-249X.

A convenient pathway to obtain 3β-hydroxy-6-oxo-5α-steroids from 3β-acetoxy Δ⁵-steroids is reported; the methodology was applied to the synthesis of laxogenin (7), substance that behaves as a plant growth hormone. This is an alternative way to produce an important functionality found in many examples of naturally occurring steroids. The developed procedure uses inexpensive reagents and can be carried out in four steps. The oxidizing and acidic steps used in this methodology did not affect the labile spiroketal side chain present in diosgenin (16).

Keywords : laxogenin; diastereoselective epoxidation; 3β-hydroxy-6-oxo-5α-steroids.

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