1986
DOI: 10.1016/s0040-4020(01)87314-2
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Syntheses of optically active pheromones with an epoxy ring, (+)-disparlure and both the enantiomers of (3z,6z)--9,10-epoxy-3,6-heneicosadiene

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Cited by 81 publications
(28 citation statements)
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“…The overall yield of 1 was 12% based on 6 (10 steps), this being considerably better than the previous result (7%). 4) The synthesis of (9S,10R)-5 is shown in Scheme 4. The side-chain triene part of 5 was prepared from 3-butyn-1-ol (17), postponing the introduction of the terminal olefin to a later stage of the synthesis.…”
Section: Resultsmentioning
confidence: 99%
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“…The overall yield of 1 was 12% based on 6 (10 steps), this being considerably better than the previous result (7%). 4) The synthesis of (9S,10R)-5 is shown in Scheme 4. The side-chain triene part of 5 was prepared from 3-butyn-1-ol (17), postponing the introduction of the terminal olefin to a later stage of the synthesis.…”
Section: Resultsmentioning
confidence: 99%
“…The synthesis of (3Z,6Z,9S,10R)-9,10-epoxy-3,6-henicosadiene (1) was first reported by Mori and Ebata in 1986 by employing Sharpless asymmetric epoxidation as the key step. 4) Similarly, by employing the same reaction, (3Z,6Z,9S,10R)-9,10-epoxy-1,3,6-henicosatriene (5) and its lower homolog (4) were synthesized in 1989.…”
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confidence: 99%
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“…This colorless oil of 7 was employed in the next step without further purification. (8). A freshly prepared solution of EtMgBr in THF (2.06M, 19.0ml, 39.1 mmol) was added dropwise to a solution of 7 (6.98 g, 39.1 mmol) in dry THF (15 ml) at room temperature under argon.…”
Section: Tetrahydro-2-(25-hexadiynyloxy)-2h-pyranmentioning
confidence: 99%
“…An epoxide hydrase (EH) is present in male and female antennae and legs of L. dispar that converts disparlure to the corresponding threo-7,8-diol (4) 1~ Moreover, the male antennal EH produced the threo-(7R,8R)-diol enantiomer stereoselectively; that is ( +)-(7R,8S)-, (-)-(7S,8R)-, and racemic disparlure were all converted to the (7R,8R)-diol with enantiomeric excesses of > 92 % as determined by analysis of the derivatized diols by chiral phase capillary gas chromatography (CP-CGC) 11. In this study, we determined the stereoselectivity of the hydration of racemic disparlure by the EH derived from male antennae (MA), male legs (ML), female antennae (FA), and female legs (FL).…”
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confidence: 99%