Method for making 3.alpha.-hydroxy, 3.beta.-substituted-pregnane

Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing

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540 6, 540 28, 540120, 540 95, 540 96, 540 99, 540108, 540109, 540114, 552508, 552539, 552544, 552546, 552552, C07J 2100, C07J 4300, C07J 4100

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053191153

ABSTRACT:
This invention provides a simplified method for converting pregnan-3,20-dione compounds to 3.alpha.-hydroxy,3.beta.-substituted-pregnanes. By selective use of reagents the unprotected dione is converted chemoselectively and diastereoselectively into a 3(R)-pregnan-3-spiro-2'oxirane-20-one intermediate. This intermediate can then be converted regioselectively by a second set of reactions to the 3.alpha.-hydroxy,3.beta.-substituted-20-one form, which can be further modified at the 20-keto position.
Through this method, each ketone group is independently treated. By modifying the ketones one at a time, one can obtain the desired stereo-specificity at each site.

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