Enantioselective synthesis of (2R,3R,7S)-3,7-dimethylpentadecan-2-ol, sex pheromone component of pine sawflies

Authors
Moreira, JA Correa, AG
Citation
Ja. Moreira et Ag. Correa, Enantioselective synthesis of (2R,3R,7S)-3,7-dimethylpentadecan-2-ol, sex pheromone component of pine sawflies, J BRAZ CHEM, 11(6), 2000, pp. 614-620
Citations number
13
Categorie Soggetti
Chemistry
Journal title
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
ISSN journal
01035053 → ACNP
Volume
11
Issue
6
Year of publication
2000
Pages
614 - 620
Database
ISI
SICI code
0103-5053(2000)11:6<614:ESO(SP>2.0.ZU;2-W
Abstract
The pine sawfly, Neodiprion sertifer (Geoffrey) (Hymenoptera: Diprionidae), is a widespread and economically important forest insect in North America, Japan and Europe. It has been demonstrated that the main sex pheromone com ponents of this species are acetate or propionate of 3,7-dimethyl-2-pentade canol (diprionol). We describe herein an enantioselective synthesis of (2R, 3R, 7S)-diprionol in 12 steps (7.5% overall yield), starting from commerci al (-)-isopulegol.