Syntheses of bioactive bisabolane-type Cryptomeria japonica sesquiterpenes.
The first diastereoselective synthesis of (1S,6R)-1-hydroxy-2,7(14),10-bisabolatrien-4-one, an antifeedant against Acusta despesta and Locusta migratoria, was produced from Cryptomeria japonica (commonly known as Japanese cedar), starting from (R)-(-)-carvone via (R)-(-)-cryptomerione. The enantiomer was transformed into (1S,3R,6R)-1-hydroxy-7(14),10-bisaboladien-4-one, a novel antifeedant against L. migratoria from the same tree, by 1,4-selective reduction of the enone moiety.
Shimizu
Nobuhiro
N
Department of Bioscience and Biotechnology, Faculty of Bioenvironmental Science, Kyoto Gakuen University, Sogabe, Kameoka, Japan. shimizu@kyotogakuen.ac.jp
Kuwahara
Yasumasa
Y
D032485:Cryptomeria / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
C541000:(1S,6R)-1-hydroxy-2,7(14),10-bisabolatrien-4-one; D012717:Sesquiterpenes