Enantiospecific Synthesis of Both Enantiomers of the Longtailed Mealybug Pheromone and Their Evaluation in a New Zealand Vineyard

The irregular monoterpenoid sex pheromone of Pseudococcus longispinus and its enantiomer were prepared from the corresponding bornyl acetates. The use of readily accessible chiral starting materials and lactone–lactone rearrangement are the highlights of the present synthesis. The biological activit...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-08, Vol.80 (15), p.7785-7789
Main Authors: Ramesh, Remya, Bell, Vaughn, Twidle, Andrew M, Gonnade, Rajesh, Reddy, D. Srinivasa
Format: Article
Language:English
Subjects:
Animals
Biological Phenomena
Hemiptera - chemistry
Lactones - chemistry
Male
New Zealand
Pheromones - chemical synthesis
Stereoisomerism
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Summary:The irregular monoterpenoid sex pheromone of Pseudococcus longispinus and its enantiomer were prepared from the corresponding bornyl acetates. The use of readily accessible chiral starting materials and lactone–lactone rearrangement are the highlights of the present synthesis. The biological activities of the two enantiomers and racemic mixture were tested in a New Zealand vineyard. The (S)-(+)-enantiomer was significantly more attractive to P. longispinus males than the racemic mixture or the (R)-(−)-enantiomer.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01131