Bioactive natural products and chirality.

Kenji Mori

Index: Chirality 23(6) , 449-62, (2011)

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Abstract

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.Copyright © 2011 Wiley-Liss, Inc.