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Asymmetric syntheses of (1R,1′R,5′R,7′R) and (1S,1′R,5′R,7′R)-1-hydroxy-exo-brevicomin and a formal synthesis of (+)-exo-brevicomin
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Mar2004, Vol. 45 Issue 10, p2227. 3p. - Publication Year :
- 2004
-
Abstract
- Asymmetric syntheses of (1R,1′R,5′R,7′R) and (1S,1′R,5′R,7′R)-1-hydroxy-exo-brevicomins 1 and 2, volatiles of the male mountain pine beetle, and a formal synthesis of (+)-exo-brevicomin 3, a component of the attracting pheromone system of several bark beetles have been achieved. The key steps are Birch reduction of commercially available α-picoline, selective Wittig olefination, and Sharpless asymmetric dihydroxylation. [Copyright &y& Elsevier]
- Subjects :
- *CHEMICAL reactions
*PHEROMONES
*HYDROXYLATION
*BIRCH reduction
Subjects
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 45
- Issue :
- 10
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 12234541
- Full Text :
- https://doi.org/10.1016/j.tetlet.2003.12.157