Synthesis of [16,16,16-2H3] 11-hexadecynoic acid and [15,15,16,16,16-2H5] (Z,Z)-11,13-hexadecadienoic acid and their use as tracers in a key step of the sex pheromone biosynthesis of the processionary moth.
✍ Scribed by Mireia Barrot; Gemma Fabriás; Francisco Camps
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 659 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Akbrt:~synthesisofdeuterhmnlsbebdll-~~acidand(ZZ)_11,13-hexadaadienr6cacid ~~ullsetaimestigatetheb~~pPthwayofthe~essimarymothsexphcrwroneis mpaled. In .[16J6.16-*H31 11-bex&kynoie acid, deutexium atoms wexe inlmdmxd by reaclkn of Moalkyne 6b with (CD3)@Li. Akylation of terminal diyne 14b witb CD3CD21 folbnved by &xeosekctive reduction of the corresponding diyne to the conesponding (225) diene afforded [15.1s.1616@&10_11,13-kx&cxWk acti GLC-MS allstyaed of exhacta flum &Wuimne Some years ago, (Z)-13-hexadccen-11-ynyl acetate (1) was identified as the major component of the fen& sex pheromone of the proccssionary moth. Thaumetopoeu pityocumpa, in this laborator$. Ongoing nseareh on the biosynthesis of this compound and other putative minor components, so far undetected in phcromonal gland sax&m, led to the cstablishmcnt of pathways depicted in Fig. 12v3. By application of SAectivcly lahclal pa#nason in in viva cxpuimmd, it was inferred that (2)-l 1-hwcadectnoic acid was formed WXWlrcooH