Synthesis of optically pure (+)-trans-verbenol and its antipode, the pheromone of Dendroctonus bark beetles.
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In this article, pure (+)-trans-Verbenol and its antipode (2b) were synthesized for the first time and their optical purities were checked by NMR as their MTPA esters (2e and 2e′, respectively).Abstract:
Pure (+)-trans-Verbenol (2b) and its antipode (2b′) were synthesized for the first time and their optical purities were checked by NMR as their MTPA esters (2e and 2e′, respectively).read more
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Journal ArticleDOI
Stereochemistry of the palladium-catalyzed allylic substitution: the syn-anti dichotomy in the formation of (π-allyl)palladium complexes and their equilibration
TL;DR: The mechanism of palladium(0)-catalyzed allylic substitution has been investigated with the aim of finding whether or not the intermediate (π-allyl)palladium complexes can arise in a syn fashion as an alternative to the well known anti-mechanism as discussed by the authors.
Journal ArticleDOI
Access to Optically Active Ipsdienol from Verbenone
Günther Ohloff,Wolfgang Giersch +1 more
TL;DR: Verbenone 1 or 2 is converted in three steps to ipsdienol 9 or 10 respectively as mentioned in this paper, and the diastereoisomeric 2(10)-pinen-4-ols 6 and 7 (or 5 and 8), wich have identical chirality at the carbon atoms bearing OH groups, afford ipsdenol 10 with the same optical purity as the starting material.
Book ChapterDOI
Insect Pheromones: A Critical Review of Recent Advances in Their Chemistry, Biology, and Application
TL;DR: The chemical basis of insect behavior is firmly established and forms an integral part of regulatory biology and part of an overall attempt to understand behavior at the molecular level.
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Stereochemistry of the verbenols
TL;DR: Nuclear magnetic resonance and chemical evidence shows that the product of lithium aluminium hydride reduction of verbenone is cis-verbenol, and that of lead tetra-acetate oxidation of α-pinene is trans-Verbenol.