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A New Synthesis of (−)‐Frontalin, the Bark Beetle Pheromone
Author(s) -
Nishimura Yutaka,
Mori Kenji
Publication year - 1998
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(199802)1998:2<233::aid-ejoc233>3.0.co;2-m
Subject(s) - chemistry , octane , pheromone , stereochemistry , enantiomer , bark beetle , yeast , bicyclic molecule , bark (sound) , enantioselective synthesis , organic chemistry , catalysis , botany , biochemistry , biology , physics , acoustics
(−)‐Frontalin [(1 S ,5 R )‐1,5‐dimethyl‐6,8‐dioxabicyclo[3.2.1]‐ octane ( 1 )] was synthesized from ethyl 2‐oxocyclopentane‐1‐carboxylate ( 2 ) as the starting material. Baker′s yeast was used for the asymmetric reduction of 2 to 3 . The S configuration at C‐1 of 1 was generated by diastereoselective methylation of the dianion derived from 3 to give 4 . The present process furnished about 10 g of 1 with enantiomeric purity of 89.1% e.e.