| Title: | Improved synthesis of three methyl-branched pheromone components produced by the female lichen moth |
| Author(s): | Taguri T; Yamakawa R; Adachi Y; Mori K; Ando T; |
| Address: | "Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology, Japan" |
| Journal Title: | Biosci Biotechnol Biochem |
| ISSN/ISBN: | 1347-6947 (Electronic) 0916-8451 (Linking) |
| Abstract: | "Female moths of Lyclene dharma dharma (Arctiidae, Lithosiinae) produce a novel sex pheromone composed of three methyl-branched ketones: 6-methyl-2-octadecanone (I), 14-methyl-2-octadecanone (II), and 6,14-dimethyl-2-octadecanone (III). Their structures were confirmed by syntheses accomplished by a different route for each component. In order to obtain a sufficient amount of the synthetic pheromone, we developed new routes via methyl-branched 1-alkenes: 6-methyl-1-octadecene (1), 14-methyl-1-octadecene (2), and 6,14-dimethyl-1-octadecene (3). Compound 1 was synthesized by coupling between a C(10)-chain bromide and a 3-methyl-branched C(8) unit (A) prepared from 3-methyl-1,5-pentanediol, 2, by coupling between a C(11)-chain bromide and a 3-methyl-branched C(7) unit (B) prepared from 2-hexanone, and 3, by connecting A and B, using propargyl alcohol as a C(3) linchpin. The use of 3-chloro-1-propanol and tert-butyl acetoacetate as the linchpin was also examined to connect the two synthetic blocks in the synthesis of 3. Components I-III were obtained by Wacker oxidation of the corresponding 1-alkenes 1-3 in good yields" |
| Keywords: | Alkenes/chemistry Animals Female Magnetic Resonance Spectroscopy Moths/*chemistry Oxidation-Reduction Sex Attractants/*chemical synthesis/chemistry; |
| Notes: | "MedlineTaguri, Tomonori Yamakawa, Rei Adachi, Yasushi Mori, Kenji Ando, Tetsu eng England 2010/01/09 Biosci Biotechnol Biochem. 2010; 74(1):119-24. doi: 10.1271/bbb.90639. Epub 2010 Jan 7" |
