title: 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.
authors.affiliation: Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA 30322, USA.
authors.forename: Daniel
authors.initials: D
authors.lastname: Morton
authors.forename: Allison R
authors.initials: AR
authors.lastname: Dick
authors.forename: Debashis
authors.initials: D
authors.lastname: Ghosh
authors.forename: Huw M L
authors.initials: HM
authors.lastname: Davies
mesh_terms: D000728:Androgens / Q000737:chemistry*; D000730:Androstadienes / Q000737:chemistry*; D002384:Catalysis; D006859:Hydrogen / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D012834:Silver / Q000737:chemistry*
chemical_list: D000728:Androgens; D000730:Androstadienes; C030011:carbene; D012834:Silver; D006859:Hydrogen; D012238:Rhodium; D008697:Methane; D010100:Oxygen