ORGN 912 |
Nakorone 3, durgamone 6 and abudinol A and B have been isolated from marine sponges of the Axinellidae family Ptilocaulis spiculifer. The characteristic structures of these terpenoids have led us to initiate a total synthesis program based on our stereoselective oxacyclizations of polyepoxides and on biomimetic polyene carbacyclizations. We have discovered that mixed diepoxide-alkene cyclizations proceed smoothly in the presence of catalytic Lewis acids TMSOTf or TBSOTf and one equivalent of DTBMP. The structures of cyclization products, tricyclic allene 2 and bicyclic ketone 5, have been verified by X-ray diffractometry. The success of this mixed oxa-carba polycyclization cascade will find many applications in the total synthesis of other terpenoid natural products with interesting biological activities. The lecture will describe the total syntheses nakorone 3 and durgamone 6 as well as our work in progress towards the syntheses of abudinol A and B.
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Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Thursday, 14 September 2006 Moscone Center -- Room 134, Oral
Division of Organic Chemistry |