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A Three-Step Route to a Tricyclic Steroid Precursor

Douglass F. Taber* and Ritesh B. Sheth

*Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, Email: taberdfudel.edu

D. F. Taber, R. B. Sheth, J. Org. Chem., 2008, 73, 8030-8032.

DOI: 10.1021/jo801767n (free Supporting Information)


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Abstract

Wittig reaction of aldehydes with (cyclopropylmethyl)triphenylphosphonium bromide delivered alkenyl cyclopropanes. UV irradiation in the presence of Fe(CO)5 converted these alkenyl cyclopropanes to 2-substituted cyclohexenones. This approach enabled a three-step synthesis of the tricyclic core of estrone methyl ether.

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estrone 3-methyl ether (CAS: 1624-62-0)



Key Words

Wittig Reaction, Cyclohexenones


ID: J42-Y2008-3030