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Absolute stereochemistry of serricornin, the sex pheromone of cigarette beetle, as determined by the synthesis of its (4S,6R,7R)-isomer

✍ 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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✦ 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 -


πŸ“œ SIMILAR VOLUMES


Determination of the absolute configurat
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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.

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## Abstract By synthesizing some isomers of 4,6,8‐trimethyl‐7,9‐undeca‐dien‐5‐ol, (4__R__\*,5__R__\*,6__S__\*,7__E__,9__E__)‐relative stereochemistry was assigned to the isomer isolated as the female specific compound of the tergal glands secretion of the woodroach __Cryptocercus punctulatus__.