ORGN 384 |
| Pyrrolizidine and indolizidine alkaloids are vast classes of natural products whose members feature an array of interesting biological properties. Our interest in certain pyrrolizidine and indolizidines and their unnatural analogs prompted us to develop a synthetic strategy which allows for variation of three structural features of the bicyclic alkaloid core (Figure). These features include saturation or unsaturation at C1-C2, size of the B-ring, and presence or absence of oxidation at C6 and/or C7. Efforts toward synthesis of the alkaloid core include the use of a microwave-assisted aza-Cope rearrangement—Mannich cyclization for the construction of the A ring and an intramolecular reductive coupling for the cyclization of the B ring. Details of the synthetic methods including optimization of the key aza-Cope—Mannich and B-ring cyclization steps will be described.
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Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster
Division of Organic Chemistry |
