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Convenient method for the functionalization of the 4- and 6-positions of the androgen skeleton.

ABSTRACT: The preparation and reactivity of steroidal vinyldiazo compounds is reported, providing a convenient, substituent tolerant, chemo- and stereoselective entry into 4- and 6-substituted androgen analogues from a common precursor. Under dirhodium catalysis, O-H insertion occurs at the carbenoid site, leading to 4-substituted steroids, but under silver catalysis, O-H insertion occurs at the vinylogous position, leading to 6-substituted steroids.

SUBMITTER: Morton D

PROVIDER: S-EPMC3357189 | biostudies-literature | 2012 Jun

REPOSITORIES: biostudies-literature

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Convenient method for the functionalization of the 4- and 6-positions of the androgen skeleton.

Morton Daniel D Dick Allison R AR Ghosh Debashis D Davies Huw M L HM

Chemical communications (Cambridge, England) 20120509 47

The preparation and reactivity of steroidal vinyldiazo compounds is reported, providing a convenient, substituent tolerant, chemo- and stereoselective entry into 4- and 6-substituted androgen analogues from a common precursor. Under dirhodium catalysis, O-H insertion occurs at the carbenoid site, leading to 4-substituted steroids, but under silver catalysis, O-H insertion occurs at the vinylogous position, leading to 6-substituted steroids. ...[more]

PMID: 22572866

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