Formal Synthesis of Sex Pheromone of Gypsy Moth (+)-Disparlure from L-(+)-Tartaric Acid

  • Gwon, Gi Baek; 
  • Kim, Hang Soo; 
  • Park, Jae Won; 
  • Choi, Jong Soo; 
  • Doh, Kyung Oh; 
  • ... Kim, Kyung Jin; 
  • 외 1명
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초록

A simple strategy for the formal synthesis of the sex pheromone of gypsy moth (+)-disparlure from L -(+)-tartaric acid is described herein. The key steps include the mono-esterification and regioselective ring -opening of an epoxide using a Grignard reagent. The strategy of conferring asymmetry using 2-butanone enables mono-esterification in high yield and reduces the number of steps. Subsequently, (+)-disparlure is synthesized via the regioselective ring opening of the epoxide.

키워드

Gypsy moth; Pheromones; (+)-Disparlure; L-Tartaric acid; Mono-esterification; CATALYZED KINETIC RESOLUTION; OPTICALLY-ACTIVE PHEROMONES; ASYMMETRIC-SYNTHESIS; ALPHA,BETA-EPOXY SULFOXIDES; ENANTIODIVERGENT SYNTHESIS; ORGANIC-SYNTHESIS; EPOXY RING; ENANTIOMERS; LIPASE; (-)-DISPARLURE
제목
Formal Synthesis of Sex Pheromone of Gypsy Moth (+)-Disparlure from L-(+)-Tartaric Acid
저자
Gwon, Gi Baek; Kim, Hang Soo; Park, Jae Won; Choi, Jong Soo; Doh, Kyung Oh; Kim, Kyung Jin; Seu, Young Bae
DOI
10.5012/jkcs.2024.68.3.131
발행일
2024-06-20
유형
Article
저널명
대한화학회지
권
68
호
3
페이지
131 ~ 134