Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm.
نویسندگان
چکیده
A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia-Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24-29% total yield via a six-step sequence. The simple scale-up strategy provides a new way to achieve the asymmetric synthesis of the sex pheromone.
منابع مشابه
New Syntheses of 1,7-Dimethylnonyl Propanoate, the Western Corn Rootworm Pheromone, in Four Different Ways via Cross Metathesis, Alkylation and Coupling ReactionsPheromone Synthesis, Part 242. See ref.1 for Part 241
A mixture of the four stereoisomers of 1,7-dimethylnonyl propanoate, the female sex pheromone of the western corn rootworm (Diabrotica virgifera virgifera LeConte), was synthesized in four different ways by employing one of the following four reactions as the key step: (i) cross metathesis using the Grubbs I catalyst, (ii) cross metathesis using the Grubbs II catalyst, (iii) alkylation of an al...
متن کاملSynthesis of the four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the screwworm fly, Cochliomyia hominivorax.
The four stereoisomers of 7-acetoxy-15-methylnonacosane (1), a component of the female sex pheromone of the New World screwworm fly (Cochliomyia hominivorax) were synthesized. The stereogenic center at C-15 of 1 originated from that of the enantiomers of citronellal, and that at C-7 was generated by lipase-catalyzed asymmetric acetylation of (3RS,11R)- and (3RS,11S)-17-methyl-1-trimethylsilylpe...
متن کاملSynthesis of Southern Corn Rootworm Pheromone from S-Citronellol and Its Field Evaluation
Southern rootworm (Diabrotica undecimpunctata howardi) affects several plants such as soybean, sorghum, wheat, cucumber, alfalfa, cucurbits and it is most damaging to corn and peanuts. The pheromone based “attract and kill” strategy is one of the powerful ways to control pest population. To address our key objective of the practical utility of the synthetic pheromone, we have developed a simple...
متن کاملStereoisomer libraries: total synthesis of all 16 stereoisomers of the pine sawfly sex pheromone by a fluorous mixture-synthesis approach.
All 16 stereoisomers of the sex pheromone of pine sawfly (3,7,11-trimethylundecanol propanoate ester) have been synthesized on a 10- to 20-mg scale by a split-parallel fluorous mixture-synthesis approach. Spectral data obtained for all 32 compounds (16 alcohols and the corresponding propionates) matched well with published data, thereby validating the fluorous-tag encoding of diastereoisomers. ...
متن کاملEffect of Seed Blends and Soil-Insecticide on Western and Northern Corn Rootworm Emergence from mCry3A+eCry3.1Ab Bt Maize.
Seed blends containing various ratios of transgenic Bt maize (Zea mays L.) expressing the mCry3A+eCry3.1Ab proteins and non-Bt maize (near-isoline maize) were deployed alone and in combination with a soil applied pyrethroid insecticide (Force CS) to evaluate the emergence of the western corn rootworm, Diabrotica virgifera virgifera LeConte, in a total of nine field environments across the Midwe...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Molecules
دوره 23 3 شماره
صفحات -
تاریخ انتشار 2018