Asymmetric Total Synthesis of (−)-Panacene and Correction of Its Relative Configuration
| Autor: | Stephen L. MacNeil, Martin Pouliot, John Boukouvalas, Joël Robichaud, Victor Snieckus |
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| Rok vydání: | 2006 |
| Předmět: |
Molecular Structure
Tandem Chemistry Organic Chemistry Absolute configuration Total synthesis Stereoisomerism General Medicine Biochemistry Catalysis Hydrocarbons Brominated Alkadienes Dual role Alkynylation Computational chemistry Intramolecular force Aplysia Animals Organic chemistry Stereoselectivity Physical and Theoretical Chemistry Palladium |
| Zdroj: | Organic Letters. 8:3597-3599 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol061385e |
| Popis: | [reaction: see text] The first synthesis of (-)-panacene has been accomplished in concise, highly stereoselective fashion from commercially available 2-methoxy-6-methylbenzoic acid (15 steps, 8.3% overall yield). The synthesis unambiguously establishes the correct relative and absolute configuration of panacene, and demonstrates the serviceability of Pd(II)-mediated tandem intramolecular alkoxycarbonylation-lactonization for the expedient assembly of its tricyclic core, and the dual role of asymmetric alkynylation as an initial source of chirality and as a powerful tool for manipulating diastereoselectivity. |
| Databáze: | OpenAIRE |
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