4.8 Article

Enantioselective Formal Synthesis of (-)-Englerin A via a Rh-Catalyzed [4+3] Cycloaddition Reaction

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ORGANIC LETTERS
卷 12, 期 16, 页码 3708-3711

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AMER CHEMICAL SOC
DOI: 10.1021/ol1015652

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  1. National Institutes of Health (NIH) [R01 GM081484-01]
  2. National Science Foundation [CHE9709183, CHE0741968]
  3. Direct For Mathematical & Physical Scien
  4. Division Of Chemistry [0741968] Funding Source: National Science Foundation

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An enantioselective formal synthesis of (-)-englerin A (1) is reported. Key to the strategy is a Rh-catalyzed [4 + 3] cycloaddition reaction between furan 10 and diazo ester 11 that, following an intramolecular aldol condensation, produces the tricyclic scaffold of englerin. This strategy also provides a rapid, efficient, and stereoselective access to the biologically significant core motif of the guaiane sesquiterpenes.

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