ORGN 889 |
| When using [Rh(CO)2Cl]2 as a CO insertion catalyst, the allenic Pauson Khand reaction selectively occurs with the distal double bond of the allene to form bicyclo[5.3.0]decanones possessing appropriately positioned double bonds suitable for the construction of natural product substructures. To further explore the synthetic utility of this method, a conceptually novel strategy for efficiently constructing complex [6-7-5] tricyclic ring structure has been proposed by incorporating a cyclohexane ring in the allenyne tether. Thus, by walking the allene and alkyne moieties around the cyclohexane ring, a variety of highly functionalized [6-7-5] tricyclic ring structures have been synthesized in a step-economical fashion. The scope and limitation of this strategy and efforts to apply the resulting tricyclic compounds to the synthesis of the core structures of natural products, such as resiniferatoxin, grayanotoxin and rippertane will be reported on.
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New Reactions and Methodology
8:00 AM-11:40 AM, Thursday, 14 September 2006 Moscone Center -- Room 133, Oral
Division of Organic Chemistry |
