A three-step route to a tricyclic steroid precursor.
2-Alkyl cyclohexenones are useful intermediates for organic synthesis. The Wittig reaction of a series of aldehydes with (cyclopropylmethyl)triphenylphosphonium bromide delivered the corresponding alkenyl cyclopropanes. UV irradiation in the presence of Fe(CO)5 converted the alkenyl cyclopropanes to the 2-substituted cyclohexenones. This approach enabled a three-step synthesis of the tricyclic core of estrone methyl ether.
Taber
Douglass F
DF
Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Sheth
Ritesh B
RB
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry; D058085:Iron Compounds / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D003521:Cyclopropanes; D058085:Iron Compounds; D007659:Ketones; D013256:Steroids; C515100:iron pentacarbonyl; C030797:cyclopropane