Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica
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 r...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2014-04-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.71 |
| id |
doaj-9abec5455f95470189c8aad9d2ae4b3a |
|---|---|
| record_format |
Article |
| spelling |
doaj-9abec5455f95470189c8aad9d2ae4b3a2021-02-02T04:44:49ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-04-0110176176610.3762/bjoc.10.711860-5397-10-71Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanicaDanny Geerdink0Jeffrey Buter1Teris A. van Beek2Adriaan J. Minnaard3Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The NetherlandsStratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The NetherlandsNatural Products Chemistry Group, Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, 6703 HB Wageningen, The NetherlandsStratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The NetherlandsVirgin 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%.https://doi.org/10.3762/bjoc.10.71asymmetric catalysiscopperdeoxypropionatesnatural productssex pheromoneTrichogramma turkestanica |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Danny Geerdink Jeffrey Buter Teris A. van Beek Adriaan J. Minnaard |
| spellingShingle |
Danny Geerdink Jeffrey Buter Teris A. van Beek Adriaan J. Minnaard Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica Beilstein Journal of Organic Chemistry asymmetric catalysis copper deoxypropionates natural products sex pheromone Trichogramma turkestanica |
| author_facet |
Danny Geerdink Jeffrey Buter Teris A. van Beek Adriaan J. Minnaard |
| author_sort |
Danny Geerdink |
| title |
Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica |
| title_short |
Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica |
| title_full |
Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica |
| title_fullStr |
Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica |
| title_full_unstemmed |
Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica |
| title_sort |
asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp trichogramma turkestanica |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2014-04-01 |
| description |
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%. |
| topic |
asymmetric catalysis copper deoxypropionates natural products sex pheromone Trichogramma turkestanica |
| url |
https://doi.org/10.3762/bjoc.10.71 |
| work_keys_str_mv |
AT dannygeerdink asymmetrictotalsynthesisofaputativesexpheromonecomponentfromtheparasitoidwasptrichogrammaturkestanica AT jeffreybuter asymmetrictotalsynthesisofaputativesexpheromonecomponentfromtheparasitoidwasptrichogrammaturkestanica AT terisavanbeek asymmetrictotalsynthesisofaputativesexpheromonecomponentfromtheparasitoidwasptrichogrammaturkestanica AT adriaanjminnaard asymmetrictotalsynthesisofaputativesexpheromonecomponentfromtheparasitoidwasptrichogrammaturkestanica |
| _version_ |
1724305067936317440 |