4.8 Article

Highly Enantioselective Total Synthesis of (-)-(3′S)-Lomatin and (+)-(3′S,4′R)-trans-Khellactone

Journal

ORGANIC LETTERS
Volume 11, Issue 9, Pages 1991-1993

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol900444h

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Funding

  1. Loughborough University
  2. University of East Anglia
  3. Charnwood Molecular Ltd

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Concise highly enantioselective three-step syntheses are described for (-)-(3'S)-lomatin and (+)-(3'S,4'R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.

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