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

被引：10

作者：

CUBERO, II

LOPEZESPINOSA, MTP

CASTILLO, RA

机构：

[1] Department of Organic Chemistry Faculty of Pharmacy, University of Granada, Granada

来源：

JOURNAL OF CHEMICAL ECOLOGY | 1992年 / 18卷 / 02期

关键词：

ENANTIOSPECIFIC SYNTHESIS; ENANTIOMERS; SPIROACETAL; PHEROMONE; DACUS-OLEAE; OLIVE FRUIT FLY; DIPTERA; TEPHRITIDAE; D-FRUCTOSE;

D O I：

10.1007/BF00993747

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of (3S,6R)-3-hydroxy-1,7-dioxaspiro[5.5]undecane (8) and its (4R)-4-hydroxy isomer (11) from (3R,4S,6R)-3,4-dihydroxy-1,7-dioxaspiro[5.5]undecane (1), obtained from D-fructose, has been accomplished by regioselective deoxygenation at C-4 and C-3, respectively, of the appropriately protected derivatives.

引用

页码：115 / 125

页数：11

共 14 条

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[4] PHEROMONES .53. SYNTHESIS OF (3S,6R)-3-HYDROXY-1,7-DIOXASPIRO [5.5]UNDECANE AND (3S,6S)-3-HYDROXY-1,7-DIOXASPIRO[5.5]UNDECANE - A COMPONENT OF OLIVE FLY PHEROMONE COMPLEX (DACUS-OLEAE)
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[5] ENANTIOSPECIFIC SYNTHESIS OF SPIROACETALS .1. AN ENANTIOSPECIFIC SYNTHESIS OF (-)-TALAROMYCIN-A AND (-)-TALAROMYCIN-B FROM D-FRUCTOSE
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LOPEZESPINOSA, MTP
[J]. CARBOHYDRATE RESEARCH, 1990, 205 : 293 - 304
[6] SYNTHETIC APPLICATION OF PARTIALLY PROTECTED FRUCTOPYRANOSES
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[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1986, 5 (02) : 299 - 311
[7] CUBERO II, 1991, IN PRESS J CHEM ECOL
[8] A GENERAL-APPROACH TO THE STEREOSELECTIVE SYNTHESIS OF SPIROKETALS - A TOTAL SYNTHESIS OF THE PHEROMONES OF THE OLIVE FRUIT-FLY AND RELATED-COMPOUNDS
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[9] SPIROKETALS - THE SYNTHESIS OF AN OLIVE FLY PHEROMONE COMPONENT, 4-HYDROXY-1,7-DIOXASPIRO[5,5]UNDECANE, VIA A NOVEL CATION-OLEFIN CYCLIZATION STEP
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[10] A NEW SYNTHESIS OF 1,7-DIOXASPIRO[5.5]UNDECANES - APPLICATION TO A RECTAL GLAND SECRETION OF THE OLIVE FRUIT-FLY (DACUS-OLEAE)
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