| Title: | Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica |
| Author(s): | Geerdink D; Buter J; van Beek TA; Minnaard AJ; |
| Address: | "Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands. Natural Products Chemistry Group, Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen, The Netherlands" |
| ISSN/ISBN: | 1860-5397 (Print) 1860-5397 (Electronic) 1860-5397 (Linking) |
| Abstract: | "Virgin females of the parasitoid wasp Trichogramma turkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S)-4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is reported as a contribution to this identification. Catalytic asymmetric conjugate addition of methylmagnesium bromide and stereoselective Horner-Wadsworth-Emmons olefinations are used as the key steps, and 2 was obtained in 16 steps with an overall yield of 4.4%" |
| Keywords: | Trichogramma turkestanica asymmetric catalysis copper deoxypropionates natural products sex pheromone; |
| Notes: | "PubMed-not-MEDLINEGeerdink, Danny Buter, Jeffrey van Beek, Teris A Minnaard, Adriaan J eng Germany 2014/04/30 Beilstein J Org Chem. 2014 Apr 2; 10:761-6. doi: 10.3762/bjoc.10.71. eCollection 2014" |
