Biomimetic Cyclization of Enamide-Containing Polyenes as a New Route to Azapolycycles |
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Authors: | Sen Stephanie E. Roach Steven L. |
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Affiliation: | Department of Chemistry, Indiana University-Purdue University at Indianapolis (IUPUI), 402 North Blackford Street, Indianapolis, Indiana 46202. |
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Abstract: | Enamide 4 was studied for its effectiveness as a polyene precursor in biomimetic cyclizations. While most conventional Lewis acids were poor cyclization promoters, FeCl(3).6H(2)O initiated the conversion of 4 into tricycles 6 and 7 in excellent yield. The two isomeric products result from the cyclization of intermediate aldehyde 5 by either a chair or boat B-ring transition state. These results suggest that enamides may be incorporated into polyene precursors for the construction of larger azapolycycles such as azasteroids. |
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