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.
Beilstein J Org Chem. 2014 Apr 2;10:761-6. doi: 10.3762/bjoc.10.71. eCollection 2014.
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%.
未充分确定身份的性信息素，由寄生蜂曲纹姬小蜂（Trichogramma turkestanica）的处女雌性产生少量的性信息素。据报道，（6S,8S,10S）-4,6,8,10-四甲基十三-2E,4E-二烯-1-醇（2）的对映选择性合成为该信息素的一种可能成分，作为该鉴定的贡献。催化不对称共轭加成甲基溴化镁和立体选择性霍纳-沃兹沃思-埃蒙斯烯烃化为关键步骤，并且 2 以 16 步总收率 4.4%获得。
