164802-20-4

Upstream product

• 917-54-4 methyllithium 
• 358374-83-1 (S)-(R)-7-Oxiranyl-heptane-1,2-diol 
• 358374-86-4 (2S,6'R)-2-(6-methyl-nonyl)-oxirane 
• 358374-94-4 (S)-2,2-Dimethyl-4-((R)-5-oxiranyl-pentyl)-[1,3]dioxolane 
• 358374-97-7 (2S,8R)-8-methylundecan-1,2-diol 
• 358374-96-6 (4S,6'R)-2,2-dimethyl-4-(6-methyl-nonyl)-[1,3]dioxolane 
• 358374-95-5 (S)-9-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-nonan-4-ol 
• 358374-87-5 (6S,12R)-12-methylpentadec-1-en-6-ol 

Relevant academic research and scientific papers

Hydrolytic kinetic resolution of terminal mono- and bis-epoxides in the synthesis of insect pheromones

Hydrolytic kinetic resolution (HKR) of functionalised epoxides using (salen)Co(OAc) complexes provides enantiomerically enriched epoxides and diols, which have been transformed into important insect sex pheromones. In this general approach, (-)-(R)- and (+)-(S)-10-methyldodecyl acetates from the smaller tea tortrix moth were obtained, as was (-)-(R)-10-methyltridecan-2-one from the southern corn rootworm. The (S)-epoxide obtained from undec-1-en-6-yne was transformed to (-)-(R)-(Z)-undec-6-en-2-ol (Nostrenol) from ant-lions. HKR of appropriate bisepoxides was also investigated, and transformations of the resulting bisepoxides and epoxydiols provided (-)-(1R,7R)-1,7-dimethylnonylpropanoate from corn rootworms, (-)-(6R,12R)-6,12-dimethylpentadecan-2-one from the female banded cucumber beetle, and (-)-(2S,11S)-2,11-diacetoxytridecane and (+)-(2S,12S)-2,12-diacetoxytridecane from female pea-midges.

Hydrolytic kinetic resolution of mono- and bisepoxides as a key step in the synthesis of insect pheromones

The synthetic utility of the readily separated epoxides, diols, epoxydiols and tetrols of high enantiomeric excesses, obtained by hydrolytic kinetic resolution (HKR) of functionalised mono- and bisepoxides with (salen)Co(OAc) complexes, is demonstrated by their efficient transformations to important insect pheromones.

Convergent Synthesis of (R,R)-6,12-Dimethylpentadecan-2-one, the Female Sex Pheromone of the Banded Cucumber Beetle by Iron Mediated Chirality Transfer

The highly convergent synthesis of (R,R)-6,12-dimethylpentadecan-2-one , the bioactive form of the sex pheromone produced by female adults of the banded cucumber beetle Diabrotica balteata LeConte, in high enantio- and diastereomeric purity (ee >/= 99percent, de >/= 98percent) and good overall yield (13 steps, 39percent) is described.The stereogenic centres were generated by nucleophilic addition of allyltrimethylsilane to an enantiopure planar chiral (?-allyl)-tetracarbonyliron(1+)-complex.