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Synthesis of (1 S ,2 S ,6 S ,10 R )‐ and (1 S ,2 R ,6 R ,10 R )‐1,2,6,10‐Tetramethyldodecyl Propanoate, the Components of the Sex Pheromone of the Pine Sawfly, Microdiprion pallipes
Author(s) -
Nakamura Yoshihide,
Mori Kenji
Publication year - 1999
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/(sici)1099-0690(199909)1999:9<2175::aid-ejoc2175>3.0.co;2-v
Subject(s) - sawfly , chemistry , sex pheromone , stereochemistry , kinetic resolution , enantioselective synthesis , pheromone , botany , organic chemistry , catalysis , biology , larva
(1 S ,2 S ,6 S ,10 R )‐ and (1 S ,2 R ,6 R ,10 R )‐1,2,6,10‐tetramethyldodecyl propanoate ( 1 and 2 ), the components of the pheromone of Microdiprion pallipes , were synthesized from two chiral and nonracemic building blocks, ( R )‐3‐ tert ‐butoxycarbonyl‐2‐methylpropanoic acid ( D ) and (2 R ,6 S )‐7‐acetoxy‐2,6‐dimethyl‐1‐heptanol ( G ), by employing lipase‐catalyzed kinetic resolution in a later step.