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Synthesis of the Insect Pheromone (2 S ,3 S ,7 RS )‐Diprionyl Acetate by Diastereoselective Protonation
Author(s) -
Ebert Sophia,
Krause Norbert
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200110)2001:20<3831::aid-ejoc3831>3.0.co;2-2
Subject(s) - chemistry , ketone , protonation , reagent , acylation , pheromone , lactone , organic chemistry , carvone , stereochemistry , medicinal chemistry , catalysis , ion , biology , chromatography , essential oil , limonene , genetics
The insect pheromone (2 S ,3 S ,7 RS )‐diprionyl acetate ( 1 ) was prepared from ( S , S )‐2,3‐dimethylcyclohexanone ( 2 ), which in turn was obtained by the 1,4‐addition of lithium dimethylcuprate to ( S )‐(+)‐carvone ( 3 ) and diastereoselective protonation of the resulting enolate with phenyl salicylate, followed by removal of the isopropenyl group and hydrogenation. Baeyer−Villiger rearrangement of ( S , S )‐ 2 and opening of the lactone ( S , S )‐ 8 with octyllithium provided the hydroxy ketone ( S , S )‐ 9 , which was transformed into the target molecule (2 S ,3 S ,7 RS )‐ 1 by carbonyl olefination with Petasis’ reagent, acylation and hydrogenation.