ORGN 121 |
| Azadirachtin is a terpenoid natural product isolated from the Indian neem tree. Its powerful insect antifeedant activity and complex structure make azadirachin 1 an attractive synthetic target. Our current synthetic strategy is highly convergent and designed to overcome the high level of steric crowding at the C8-C14 centres: O–alkylation of decalin 5 with propargylic mesylate 6 is envisaged to introduce intramolecularity prior to the formation of this bond. Claisen rearrangement will forge the C8-C14 linkage in the generation of allene 3 which in turn acts as a radical terminus to deliver the alkene 2 and provide the complete carbon framework of azadirachtin 1. Syntheses of the key fragments 5 & 6 are presented along with recent developments in the end game of the synthesis.
|
|
Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
