Reductive elimination of acetonides, cyclic carbonates, or cyclic sulfites of γ,δ-dihydroxy (E)-α,β-unsaturated esters: an efficient route to δ-hydroxy (E)-β,γ-unsaturated esters and δ-hydroxy esters
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 1,p. 9-10
- https://doi.org/10.1039/p19930000009
Abstract
The acetonides, cyclic carbonates, or cyclic sulfites of γ,δ-dihydroxy (E)-α,β-unsaturated esters have been found to undergo facile reductive cleavage with samarium diiodide or magnesium in methanol to provide δ-hydroxy (E)-β,γ-unsaturated esters or δ-hydroxy esters, respectively. Using the δ-hydroxy ester 3b as a chiral synthon, (–)-5-hexadecanolide, the pheromone of the oriental hornet Vespa orientalis was synthesized.Keywords
This publication has 18 references indexed in Scilit:
- Application of lanthanide reagents in organic synthesisChemical Reviews, 1992
- A simple and efficient preparation of sulfinyl chlorides from disulfides and sulfuryl chlorideTetrahedron Letters, 1986
- Lanthanides in organic synthesis. 5. Reduction of vinyloxiranes with samarium diiodide. An efficient route to functionalized chiral, non-racemic (E)-allylic alcoholsThe Journal of Organic Chemistry, 1986
- SYNTHESIS OF OPTICALLY PURE (R)- AND (S)-5-n-HEXADECANOLIDE. A PROPOSED PHEROMONE COMPONENT FROM ORIENTAL HORNETChemistry Letters, 1984
- Synthese enantiospecifique du 5-hexadecanolide, pheromone de “Vespa Orientalis”Tetrahedron, 1984
- Synthesis of the two enantiomeric forms of 5-hexadecanolide proposed pheromone component from Vespa orientalisTetrahedron Letters, 1983
- Selective alkylation of diethyl 3-oxoglutarate. Part IX. Synthesis of racemates and (+)-enantiomers of .GAMMA.-caprolactone, .GAMMA.-dodecanolactone and .DELTA.-hexadecanolactone, lactonic sex pheromones of the dermestid beetle, rove beetle and Oriental hornet.Agricultural and Biological Chemistry, 1983
- Asymmetric synthesis of five- and six-membered lactones from chiral sulfoxides: application to the asymmetric synthesis of insect pheromones, (R)-(+)-.delta.-n-hexadecanolactone and (R)-(+)-.gamma.-n-dodecanolactoneThe Journal of Organic Chemistry, 1982
- Broad-spectrum synthesis of enantiomerically pure lactones. 1. Synthesis of sex pheromones of the carpenter bee, rove beetle, Japanese beetle, black-tailed deer, and Oriental hornetThe Journal of Organic Chemistry, 1979
- Synthesis of optically active .delta.-n-hexadecalactone, the proposed pheromone from Vespa orientalisThe Journal of Organic Chemistry, 1976