Synthesis of an azasteroid using an acyl iminium ion-initiated tandem cyclization

A. G. Romero, J. A. Leiby, S. A. Mizsak

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Abstract

An acyl iminium ion-initiated tandem cyclization gave an unexpected dienone product, a secoazasteroid (2). The factors governing the formation of 2 were investigated in an attempt to optimize its formation. The reaction was applied to a more elaborate system, resulting in the synthesis of the full steroid skeleton of 13-azaandrosta-1,4-diene-3,17-dione (3), which contains the unusual substitution of a chlorine atom for the axial 19-methyl.

Original languageEnglish
Pages (from-to)6974-6979
Number of pages6
JournalJournal of Organic Chemistry
Volume61
Issue number20
DOIs
StatePublished - Jan 1 1996

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