CHEMICO-ENZYMATIC SYNTHESES OF RACEMIC AND CHIRAL ISOMERS OF 7-METHYL-1,6-DIOXASPIRO[4.5]DECANE

被引:18
作者
RAMASWAMY, S
OEHLSCHLAGER, AC
机构
[1] Department of Chemistry Simon Fraser University Burnaby
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/S0040-4020(01)86372-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Porcine pancreatic lipase (PPL) mediated resolution of 6-heptene-2-ol afforded the enantiomers in high optical purities. Alkylation products of the dianion of the 2-4'-hydroxypentyl-1,3-dithiane prepared from the enantiomers, followed by alkylative hydrolysis, afforded 97% optically pure E-7-methyl-1,6-dioxaspiro[4.5]decane.
引用
收藏
页码:1157 / 1162
页数:6
相关论文
共 21 条
[1]  
AUDIN P, 1984, B SOC CHIM FR, V2, P297
[2]   IDENTIFICATION AND SYNTHESIS OF THE MAJOR SEX-PHEROMONE OF THE OLIVE FLY (DACUS-OLEAE) [J].
BAKER, R ;
HERBERT, R ;
HOWSE, PE ;
JONES, OT ;
FRANCKE, W ;
REITH, W .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (02) :52-53
[3]  
CHEN CS, 1982, J AM CHEM SOC, V104, P7284
[4]   ALDEHYDES AND KETONES FROM THIOACETALS [J].
FETIZON, M ;
JURION, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (07) :382-&
[5]   SPIROKETALS IN THE MANDIBULAR GLANDS OF ANDRENA BEES [J].
FRANCKE, W ;
REITH, W ;
BERGSTROM, G ;
TENGO, J .
NATURWISSENSCHAFTEN, 1980, 67 (03) :149-150
[6]   2-ETHYL-1,6-DIOXASPIRO[4.4]NONANE, PRINCIPAL AGGREGATION PHEROMONE OF PITYOGENES-CHALCOGRAPHUS (L) [J].
FRANCKE, W ;
HEEMANN, V ;
GERKEN, B ;
RENWICK, JAA ;
VITE, JP .
NATURWISSENSCHAFTEN, 1977, 64 (11) :590-591
[7]   METHYL-1,6-DIOXASPIRO[4.5]DECANES AS ODORS OF PARAVESPULA-VULGARIS (L) [J].
FRANCKE, W ;
REITH, W ;
HINDORF, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (11) :862-862
[8]   DETERMINATION OF RELATIVE CONFIGURATIONS OF SPIROACETALS BY H-1-C-NMR AND C-13-NMR-SPECTROSCOPY [J].
FRANCKE, W ;
REITH, W ;
SINNWELL, V .
CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (08) :2686-2693
[9]  
FRANCKE W, 1981, Z NATURFORSCH C, V36, P928
[10]  
GRUMMITT O, 1963, ORG SYNTH, V4, P748