Absolute stereochemistry of serricornin, the sex pheromone of cigarette beetle, as determined by the synthesis of its (4S,6R,7R)-isomer
β Scribed by Masataka Mori; Tatsuji Chuman; Masahiro Kohno; Kunio Kato; Masao Noguchi; Hiroko Nomi; Kenji Mori
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- French
- Weight
- 197 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
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 -
π SIMILAR VOLUMES
The absolute configuration at C-6 and C-7 of serricornin was established as (6S, 75) by synthesizing its (65, 7S)-erythro and (6R, 7R)threo isomers.
ratceived in WK for publieatian 22 Ear& 1976) f+)-Ipsdienol is one of the aggregation pheromones of a bark beetle, Ip8 paraconfusus Lanier.lr' The structure (2 proposed for it on the basis of spectral data was confirmed by syntheses
## Abstract By synthesizing some isomers of 4,6,8βtrimethylβ7,9βundecaβdienβ5βol, (4__R__\*,5__R__\*,6__S__\*,7__E__,9__E__)βrelative stereochemistry was assigned to the isomer isolated as the female specific compound of the tergal glands secretion of the woodroach __Cryptocercus punctulatus__.