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A three-step route to a tricyclic steroid precursor.

ABSTRACT: 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.

SUBMITTER: Taber DF

PROVIDER: S-EPMC2654412 | biostudies-literature | 2008 Oct

REPOSITORIES: biostudies-literature

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A three-step route to a tricyclic steroid precursor.

Taber Douglass F DF Sheth Ritesh B RB

The Journal of organic chemistry 20080925 20

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. ...[more]

PMID: 18816101

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