Title: Applications of high-potential quinones. Part VII. The synthesis of steroidal phenanthrenes by double methyl migration
Abstract: Steroidal phenanthrenes are formed from 17 α-methyl-Δ9(11)-testosterones by the action of dichlorodicyanobenzoquinone and toluene-p-sulphonic acid in refluxing dioxan. Initial dehydration occurs without rearrangement to give δ16-derivatives, which undergo double methyl migration and oxidation to the phenanthrenes. Isolation of the Δ16-intermediates is ascribed to the presence of the Δ9(11)-bond, which eliminates the usual 11 β-H–13-Me diaxial interaction in ring C.
Publication Year: 1971
Publication Date: 1971-01-01
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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Cited By Count: 8
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