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 language | English |
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Pages (from-to) | 6974-6979 |
Number of pages | 6 |
Journal | Journal of Organic Chemistry |
Volume | 61 |
Issue number | 20 |
DOIs | |
State | Published - Jan 1 1996 |