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A stereoselective synthesis of “natural” (4S,6S,7S)-serricornin, the sex pheromone of cigarette bettle, from levoglucosenone

✍ Scribed by Masataka Mori; Tatsuji Chuman; Kunio Katō; Kenji Mori

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
231 KB
Volume
23
Category
Article
ISSN
0040-4039

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Absolute stereochemistry of serricornin,
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## 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 -

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## Abstract Faranal (1), the trail‐following pheromone of the worker of Pharaoh's ant (__Monomorium pharaonis__), was synthesized by the coupling reaction of the iododiene 3 with the chiral building block 8 as the key step. The geometrically pure iododiene 3 was prepared by the zirconocene‐mediated