Synthesis of (1R,3S,5S)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the male pheromone of a hepialid moth Endoclita excrescens, and its enantiomer

被引：2

作者：

Marukawa, K ^{[1
]}

Mori, K ^{[1
]}

机构：

[1] Sci Univ Tokyo, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

CHEMISTRY LETTERS | 2002年 / 01期

关键词：

D O I：

10.1246/cl.2002.40

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Both (1R,3S,5S)- and (1S,3R,5R)-isomers of 1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene were synthesized by starting from (S)- and (R)-isomers of ethyl 3-hydroxybutanoate, respectively. The (1R,3S,5S)-isomer was identified as the male sex pheromone of a Japanese hepialid moth, Endoclita excrescens.

引用

页码：40 / 41

页数：2

共 50 条

[1] Pheromone synthesis.: Part CCXVIII.: Synthesis of (1R,3S,5S)-1,3,8-trimethyl-2,9-dioxabicyclo[3.3.1]non-7-ene, the male pheromone of a hepialid moth, Endoclita excrescens, and its enantiomer
Marukawa, K
Mori, K
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (23) : 3974 - 3978
[2] ENANTIOSPECIFIC SYNTHESIS OF (-)-(1S,3R,5R)-1,8-DIMETHYL-3-ETHYL-2,9-DIOXABICYCLO[3.3.1]NON-7-ENE
KALLIMOPOULOS, T
DESCHENAUX, PF
JACOTGUILLARMOD, A
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[3] ENANTIOSPECIFIC SYNTHESIS OF (-)-(1R,3R,5S)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE
MASONI, C
DESCHENAUX, PF
KALLIMOPOULOS, T
JACOTGUILLARMOD, A
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[4] STEREOSELECTIVE SYNTHESIS OF (1R,3R,5S)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE
NAKATA, T
NAGAO, S
TAKAO, S
TANAKA, T
OISHI, T
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[5] STEREOSELECTIVE SYNTHESIS OF (1R,3R,5S)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE
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KUHARA, M
SUZUKI, M
CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (04) : 1078 - 1079
[6] STEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF (-)-(1R,3R,5S)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE
BLOCH, R
SECK, M
TETRAHEDRON-ASYMMETRY, 1990, 1 (12) : 855 - 856
[7] SYNTHETIC UTILITY OF CHIRAL TETRAHYDROFURANS - PREPARATION OF (1R,3R,5S)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE
GUINDON, Y
STDENIS, Y
DAIGNEAULT, S
MORTON, HE
TETRAHEDRON LETTERS, 1986, 27 (11) : 1237 - 1240
[8] FACILE CONSTRUCTION OF OPTICALLY-ACTIVE 1,3-DIOLS - SYNTHESIS OF (2S,4R)-7-OCTENE-2,4-DIOL AND ENDO-(1S,3S,5R)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE AND EXO-(1R,3S,5S)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE
CHIKASHITA, H
KITTAKA, E
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ITOH, K
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (03) : 833 - 837
[9] A SHORT, EFFICIENT SYNTHESIS OF (1S,3S,5R) AND (1S,3R,5R)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]-GNONANE
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JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22): : 5021 - 5022
[10] ASYMMETRIC-SYNTHESIS OF (1S,3S,5R)-1,3-DIMETHYL-2,9-DIOXABICYCLO[3.3.1]NONANE MEDIATED BY FERMENTING BAKERS-YEAST
OHTA, H
OZAKI, K
TSUCHIHASHI, G
CHEMISTRY LETTERS, 1987, (11) : 2225 - 2226

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