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)
see article for more reactions
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.
see article for more examples
estrone 3-methyl ether (CAS: 1624-62-0)