STEREOSPECIFIC REDUCTION OF SAPOGEN-3-ONES

STEREOSPECIFIC REDUCTION OF SAPOGEN-3-ONES

A method to stereospecifically prepare a steroidal sapogenin or a derivative thereof by reducing a 3-keto,5 -H steroidal sapogenin with a hindered organoborane or an organo-aluminium hydride. A 3 -hydroxy,5 -H steroidal sapogenin or derivative thereof may be prepared by reducing the 3-keto,5 -H ster...

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Hauptverfasser: TIFFIN, PETER, DAVID, GUNNING, PHILIP, JAMES
Format: Patent
Sprache:eng ; fre ; ger
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CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
STEROIDS
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GUNNING, PHILIP, JAMES
description A method to stereospecifically prepare a steroidal sapogenin or a derivative thereof by reducing a 3-keto,5 -H steroidal sapogenin with a hindered organoborane or an organo-aluminium hydride. A 3 -hydroxy,5 -H steroidal sapogenin or derivative thereof may be prepared by reducing the 3-keto,5 -H steroidal sapogenin using as reducing agent a relatively highly hindered organoborane reagent or by SN 2 inversion of a 3α-hydroxy,5 -H steroidal sapogenin or derivative thereof. The organo-aluminium hydride may be used to prepare a 3α,5 -H steroidal sapogenin or derivative thereof. The invention provides a convenient route to useful steroidal sapogenins such as sarsasapogenin, episarsasapogenin, smilagenin, epismilagenin and esters thereof, from readily available or easily preparable starting materials (e.g. diosgenone, preparable from diosgenin).
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subjects CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
STEROIDS
title STEREOSPECIFIC REDUCTION OF SAPOGEN-3-ONES
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