Organic compounds -- part of the class 532-570 series – Organic compounds – Cyclopentanohydrophenanthrene ring system containing
Patent
1992-03-04
1994-06-07
Tsang, Cecilia
Organic compounds -- part of the class 532-570 series
Organic compounds
Cyclopentanohydrophenanthrene ring system containing
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
Patent
active
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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Bolger Michael
Buswell Richard
Gabriel Richard
Stearns Jay
Tahir Hasan
Cocensys Inc.
Tsang Cecilia
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