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Transformation of Esters into 2‐Substituted Allyl Halides via Tertiary Cyclopropanols: Application in the Stereoselective Synthesis of (2 S ,3 S ,7 S )‐3,7‐Dimethyl‐2‐pentadecyl Acetate, the Sex Pheromone of the Pine Sawfly Neodiprion sertifer
Author(s) -
Bekish Andrei V.,
Prokhorevich Konstantin N.,
Kulinkovich Oleg G.
Publication year - 2006
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/ejoc.200600481
Subject(s) - chemistry , stereoselectivity , sawfly , halide , transformation (genetics) , stereochemistry , medicinal chemistry , organic chemistry , catalysis , botany , biochemistry , hymenoptera , gene , biology
(2 S ,3 S ,7 S )‐3,7‐Dimethyl‐2‐pentadecyl acetate ( ac‐1 ), the sex pheromone of the pine sawfly Neodiprion sertifer , has been newly synthesized by the transformation of the corresponding esters 8 and 12 into 2‐oxyalkyl‐substituted allyl bromides 4 and 5 via tertiary cyclopropanols 6 and 7 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)