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- Title
Practical Synthesis of (9 S,10 R)-9,10-epoxy-(3 Z,6 Z)-henicosadiene: The Major Pheromone of the Saltmarsh Caterpillar moth Estigmene acrea.
- Authors
Kumar, Deepak; Chirumarry, Sridhar; Vijaykumar, B. V. D.; Harshavardhan, S. J.; Shin, Dong-Soo; Jang, Kiwan; Lee, Dong-Ha
- Abstract
An efficient synthesis of (3 Z,6 Z)- cis-9,10-epoxy-3,6-henicosadiene ( 1), the major component of sex pheromone of saltmarsh caterpillar moth Estigmene acrea (Drury), was accomplished from commercially available pentadec-3-yn-1-ol and bromoundecane. Chirality was introduced by employing Sharpless asymmetric dihydroxylation on cis-olefin intermediate in the synthesis of 1, for the first time. The other key reactions include metal-dissolving coupling, Lindlar's catalyst-assisted partial hydrogenation, one-pot, three-step epoxidation from vicinal diol, and Wittig olefination. The overall yield of 1 was 24.7% in eight steps. The efficiency and simplicity of this synthesis allow the potential use of pheromone 1 in pest management programs.
- Subjects
PHEROMONES; CATERPILLARS; DIOLEFINS synthesis; OLEFINATION reactions; WITTIG reaction; ASYMMETRIC synthesis; CHIRALITY; HYDROXYLATION
- Publication
Bulletin of the Korean Chemical Society, 2015, Vol 36, Issue 4, p1245
- ISSN
0253-2964
- Publication type
Article
- DOI
10.1002/bkcs.10240