title: Bioactive natural products and chirality.
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.
authors.affiliation: Photosensitive Materials Research Center, Toyo Gosei Co., Ltd., Wakahagi, Inzai-shi, Chiba, Japan. kjk-mori@arion.ocn.ne.jp
authors.forename: Kenji
authors.initials: K
authors.lastname: Mori
mesh_terms: D000818:Animals; D001688:Biological Products / Q000737:chemistry*; D001517:Coleoptera; D005260:Female; D049673:History, 20th Century; D007536:Isomerism; D008297:Male; D015394:Molecular Structure; D000442:Octanols / Q000737:chemistry*; D010675:Pheromones / Q000138:chemical synthesis / Q000737:chemistry* / Q000502:physiology; D012724:Sex Attractants / Q000138:chemical synthesis / Q000737:chemistry* / Q000502:physiology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D033621:Tephritidae
chemical_list: D001688:Biological Products; D000442:Octanols; D010675:Pheromones; D012724:Sex Attractants; C009344:sulcatol