Syntheses of both enantiomers of 1,7-dioxaspiro[5.5]undecane:: Pheromone components of the olive fruit-fly Dacus oleae from a new chiral intermediate, the (Ss)-2-(p-tolylsulfinyl)prop-2-en-1-ol

被引：0

作者：

Hayes, P ^{[1
]}

Maignan, C ^{[1
]}

机构：

[1] Fac Sci, CNRS, Synth Organ Lab, F-72085 Le Mans 9, France

来源：

SYNTHESIS-STUTTGART | 1999年 / 05期

关键词：

insect pheromone; hetero Diels-Alder reaction; chiral 1,7-dioxaspiro[5.5]undecane; chiral sulfinyl heterodiene; (Ss)-2-(p-tolylsulfinyl)prop-2-en-1-ol;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both enantiomers of 1,7-dioxaspiro[5.5]undecane, the pheromone components of the olive fruit-fly Dacus oleae have been synthesized from a new chiral sulfoxide, (Ss)-2-(p-toylsulfinyl)prop-2-en-1-ol via hetero Diels-Alder reaction, chromatographic separation of the diastereomers on a silica gel column and desulfurization over Raney nickel as key steps.

引用

页码：783 / 786

页数：4

共 7 条

[1] PHEROMONE SYNTHESIS .79. SYNTHESIS OF THE ENANTIOMERS OF 1,7-DIOXASPIRO[5.5]UNDECANE, 4-HYDROXY-1,7-DIOXASPIRO[5.5]UNDECANE AND 3-HYDROXY-1,7-DIOXASPIRO[5.5]UNDECANE, THE COMPONENTS OF THE OLIVE FRUIT-FLY PHEROMONE
MORI, K
WATANABE, H
YANAGI, K
MINOBE, M
TETRAHEDRON, 1985, 41 (18) : 3663 - 3672
[2] A NEW SYNTHESIS OF 1,7-DIOXASPIRO[5.5]UNDECANES - APPLICATION TO A RECTAL GLAND SECRETION OF THE OLIVE FRUIT-FLY (DACUS-OLEAE)
KOCIENSKI, P
YEATES, C
TETRAHEDRON LETTERS, 1983, 24 (36) : 3905 - 3906
[3] ENANTIOSPECIFIC SYNTHESIS OF (R)-1,7-DIOXASPIRO [5.5]UNDECANE [MAJOR COMPONENT OF OLIVE FRUIT-FLY (DACUS-OLEAE) SEX-PHEROMONE] FROM D-FRUCTOSE
CUBERO, II
LOPEZESPINOSA, MTP
CASTILLO, RA
JOURNAL OF CHEMICAL ECOLOGY, 1991, 17 (08) : 1529 - 1541
[4] Sex pheromone biosynthesis in the female olive fruit-fly.: Double labelling from [18O2]-dioxygen into 1,7-dioxaspiro[5.5]undecane
Fletcher, MT
Mazomenos, BE
Georgakopoulos, JH
Konstantopoulou, MA
Wood, BJ
De Voss, JJ
Kitching, W
CHEMICAL COMMUNICATIONS, 2002, (12) : 1302 - 1303
[5] BIOSYNTHESIS OF A PHEROMONE, 1,7-DIOXASPIRO[5,5]UNDECANE, FROM C-14 SUBSTRATES INVIVO AND BY EXPLANTED FEMALE RECTAL GLANDS OF THE OLIVE FRUIT-FLY, DACUS-OLEAE (GMEL) - A PRELIMINARY-STUDY
POMONIS, JG
MAZOMENOS, BE
INTERNATIONAL JOURNAL OF INVERTEBRATE REPRODUCTION AND DEVELOPMENT, 1986, 10 (02): : 169 - 177
[6] ENANTIOSPECIFIC SYNTHESIS OF (3S,6R)-3-HYDROXY-1,7-DIOXASPIRO[5.5]UNDECANE AND ITS (4R)-4-HYDROXY ISOMER [MINOR COMPONENTS OF OLIVE FRUIT-FLY (DACUS-OLEAE) SEX-PHEROMONE
CUBERO, II
LOPEZESPINOSA, MTP
CASTILLO, RA
JOURNAL OF CHEMICAL ECOLOGY, 1992, 18 (02) : 115 - 125
[7] Non-covalent interactions in the crystallization of the enantiomers of 1,7-dioxaspiro[5.5]undecane (olive fly sex pheromone) by enantiospecific cyclodextrin hosts, hexakis(2,3,6-tri-O-methyl)-α-cyclodextrin and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin
Makedonopoulou, S
Yannakopoulou, K
Mentzafos, D
Lamzin, V
Popov, A
Mavridis, IM
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2001, 57 (57) : 399 - 409

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