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Bioactive natural products and chirality
Author(s) -
Mori Kenji
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20930
Subject(s) - chemistry , sex pheromone , enantioselective synthesis , chirality (physics) , pheromone , ambrosia beetle , stereochemistry , natural materials , organic chemistry , botany , catalysis , curculionidae , chiral symmetry breaking , physics , quantum mechanics , polymer science , nambu–jona lasinio model , biology , quark
Mori's synthetic works on bioactive natural products in general and pheromones in particular started about 40 years ago to establish their absolute configurations and also to clarify their stereochemistry–bioactivity relationships. Results indicate that bioactive natural products are not always enantiomerically pure, and the stereochemistry–bioactivity relationships are not simple but complicated. For example, neither ( R )‐ nor ( S )‐sulcatol, the aggregation pheromone of an ambrosia beetle, is behaviorally bioactive, whereas their mixture is active. In the case of olean, the sex pheromone of the olive fruit fly, its ( R )‐isomer is active against the males and the ( S )‐isomer is active against the females. Recent synthesis of two new insect pheromones is discussed to illustrate the modern methods in enantioselective synthesis. Chirality, 2011. © 2011 Wiley‐Liss, Inc.