A CONVENIENT SYNTHESIS OF (2R,8R)-8-METHYL-2-DECANOL AND ITS 2S EPIMER, THE PARENT ALCOHOLS OF ROOTWORM PHEROMONES

被引：3

作者：

CHATTOPADHYAY, S ^{[1
]}

MAMDAPUR, VR ^{[1
]}

CHADHA, MS ^{[1
]}

机构：

[1] BHABHA ATOM RES CTR,DIV BIOORGAN,BOMBAY 400085,INDIA

来源：

CHIRALITY | 1991年 / 3卷 / 01期

关键词：

DIABROTICA; STEREOCONTROL; INVERSION; TEMPLATE; CHIRAL BUILDING BLOCKS;

D O I：

10.1002/chir.530030114

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A highly stereospecific synthesis of the title compound (2R,8R)-8-methyl-2-decanol (I) has been devised via 16 simple steps. The required chirons (5 and 11) were prepared from easily accessible templates viz. (R)-methyl citronellate and (S)-glutamic acid. This on Grignard coupling furnished the ketal (12) which was converted to the desired epoxide (14) and subsequently reduced to furnish the alcohol (2R,8R)-I. Its corresponding (2S)-epimer was prepared by total stereoselective inversion of its C-2 center. The title compounds are the parent alcohols of the pheromone components of the female rootworms.

引用

页码：84 / 87

页数：4

共 14 条

[1] REACTION OF NITROUS ACID WITH GLUTAMINE AND GLUTAMIC ACID [J].

AUSTIN, AT ;

HOWARD, J .

JOURNAL OF THE CHEMICAL SOCIETY, 1961, (SEP) :3593-&

[2] CHIRAL SYNTHESIS OF TROGODERMAL, THE PHEROMONE OF DERMESTID BEETLES [J].

CHATTOPADHYAY, S ;

MAMDAPUR, VR ;

CHADHA, MS .

SYNTHETIC COMMUNICATIONS, 1990, 20 (06) :825-837

[3] PERSULFATE SILVER ION DECARBOXYLATION OF CARBOXYLIC-ACIDS - PREPARATION OF ALKANES, ALKENES, AND ALCOHOLS [J].

FRISTAD, WE ;

FRY, MA ;

KLANG, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) :3575-3577

[4] IDENTIFICATION OF A FEMALE-PRODUCED SEX-PHEROMONE OF THE WESTERN CORN-ROOTWORM [J].

GUSS, PL ;

TUMLINSON, JH ;

SONNET, PE ;

PROVEAUX, AT .

JOURNAL OF CHEMICAL ECOLOGY, 1982, 8 (02) :545-556

[5] TOSYLATION OF ALCOHOLS [J].

KABALKA, GW ;

VARMA, M ;

VARMA, RS ;

SRIVASTAVA, PC ;

KNAPP, FF .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) :2386-2388

[6]

KAULEN J, 1987, ANGEW CHEM INT EDIT, P773

[7] ENANTIOSPECIFIC SYNTHESIS OF 5-HEXADECANOLIDE, A PHEROMONE OF VESPA-ORIENTALIS [J].

LARCHEVEQUE, M ;

LALANDE, J .

TETRAHEDRON, 1984, 40 (06) :1061-1065

[8] PHEROMONE SYNTHESIS .60. SYNTHESIS OF THE PROPIONATES OF (2R, 8R)-8-METHYL-2-DECANOL AND (2S, 8R)-8-METHYL-2-DECANOL, THE PHEROMONE OF THE WESTERN CORN-ROOTWORM, EMPLOYING CHIRAL COMPOUNDS OF MICROBIAL ORIGIN AS STARTING MATERIALS [J].

MORI, K ;

WATANABE, H .

TETRAHEDRON, 1984, 40 (02) :299-303

[9] PHEROMONE SYNTHESIS .23. SYNTHESIS OF OPTICALLY-ACTIVE FORMS OF (Z)-14-METHYLHEXADEC-8-ENAL - PHEROMONE OF FEMALE DERMESTID BEETLE [J].

MORI, K ;

SUGURO, T ;

UCHIDA, M .

TETRAHEDRON, 1978, 34 (20) :3119-3123

[10] SYNTHESIS OF ENANTIOMERS OF 4-SUBSTITUTED GAMMA-LACTONES WITH KNOWN ABSOLUTE-CONFIGURATION [J].

RAVID, U ;

SMITH, LR ;

SILVERSTEIN, RM .

TETRAHEDRON, 1978, 34 (10) :1449-1452

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