A formal and enantioselective synthesis of (−)-serricornin, the sex pheromone of the cigarette beetle (lasioderma serricorne F.)
✍ Scribed by J. Tércio; B. Ferreira; Jacqueline A. Marques; J.P. Marino
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- English
- Weight
- 515 KB
- Volume
- 5
- Category
- Article
- ISSN
- 0957-4166
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📜 SIMILAR VOLUMES
4RS,6S,7S)-7-hydroxy-4.6-dimethyl-3-nonanone (serricomin and its C4epimez) may be prepared from oxazolidinone 5 in 8 steps with an overall yield of 33%.
A structure of the sex pheromone produced by the female cigarette beetle (Lasioderma serricorne F.) is established as 4,6-dimethyl-7-hydroxy-nonan-3-one (Ia) by chemical and spectroscopic evidences.
## Sumnary: The absolute stereochemistry of serricornin was determined to be (4S,6S,7S) by the synthesis of its (4S,6R,7R)-isomer using a carbohydrate synthon. ## Serricornin (la)[ 4,6-dimethyl-7-hydroxynonan-3-one ] is the sex pheromone of the female -