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Use of the carbopalladation of 1,2-propadiene in a two step synthesis of steroids

✍ Scribed by Véronique Gauthier; Bernard Cazes; Jacques Gore


Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
239 KB
Volume
32
Category
Article
ISSN
0040-4039

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✦ Synopsis


ESCLL Abstrru;f. The palladium-catalyzed reaction of 12-propadiene , the enol triflate of an atetralone and the enolate of 2-methyl-1,3-cyclopentanedione leads to compounds such as b which are transformed under acidic conditions to steroidal trienones. This approach to the steroid skeleton is presently hrnited to compounds having an aromatic A-ring.


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The reactions of ketones 1a -o, nitromethane 2, and a stoichiometric amount of piperidine 3a or ethylenediamine 3b in the presence of mercaptan 6a in THF or CH 3 CN solution give high yields of b-nitrosulfides 7a -o. The latter can be oxidized by 8a (m-CPBA or m-CPBA/AcOH) at 08C, 8b (H 2 O 2 /AcOH)