Enzymatic desymmetrization of meso-2,6-dimethyl-1,7-heptanediol. Enantioselective formal synthesis of the vitamin E side chain and the insect pheromone tribolure

被引：28

作者：

Chenevert, R

Desjardins, M

机构：

[1] Département de Chimie, Fac. des Sci. et de Genie, Université Laval, Québec

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 04期

关键词：

D O I：

10.1021/jo9516650

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral syn-1,5-dimethylalkyl subunit is found in many natural products with significant biological activities. Enzymatic esterification of meso-2,6-dimethyl-1,7-heptanediol with isopropenyl acetate in the presence of Pseudomonas cepacia lipase in organic medium provided the chiral nonracemic monoester in high enantiomeric excess (ee = 95%). This chiral building block was used in the formal syntheses of vitamin E side chain and the insect pheromone tribolure.

引用

收藏

页码：1219 / 1222

页数：4

相关论文

共 45 条

[11]

Connolly JD, 1991, DICT TERPENOIDS, V2

[12] MECHANISM OF ACTION OF VITAMIN-K [J].

DOWD, P ;

HERSHLINE, R ;

HAM, SW ;

NAGANATHAN, S .

NATURAL PRODUCT REPORTS, 1994, 11 (03) :251-264

[13] EFFICIENT STEREOSELECTIVE SYNTHESIS OF NATURAL ALPHA-TOCOPHEROL (VITAMIN-E) [J].

FUGANTI, C ;

GRASSELLI, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (22) :995-997

[14] BAKERS-YEAST MEDIATED PREPARATION OF (S)-3-(2-FURYL)-2-METHYLPROPAN-1-OL, A BIFUNCTIONAL CHIRAL-C-S ISOPRENOID SYNTHON - SYNTHESIS OF (4R,8R)-4,8-DIMETHYLDECANAL, A PHEROMONE OF TRIBOLIUM-CASTANEUM [J].

FUGANTI, C ;

GRASSELLI, P ;

SERVI, S ;

HOGBERG, HE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12) :3061-3065

[15] A STEREOCONTROLLED TOTAL SYNTHESIS OF OPTICALLY-ACTIVE (R,R)-PHYTOL [J].

FUJISAWA, T ;

SATO, T ;

KAWARA, T ;

OHASHI, K .

TETRAHEDRON LETTERS, 1981, 22 (48) :4823-4826

[16] UNPRECEDENTED REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN THE ADDITION OF ORGANO-ALUMINUM REAGENTS TO CHIRAL ALPHA,BETA-UNSATURATED ACETALS [J].

FUJIWARA, J ;

FUKUTANI, Y ;

HASEGAWA, M ;

MARUOKA, K ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :5004-5005

[17] STEREOCONTROLLED SYNTHESIS OF HIGHLY OXYGENATED ACYCLIC SYSTEMS VIA THE ENOLATE CLAISEN REARRANGEMENT OF O-PROTECTED ALLYLIC GLYCOLATES [J].

GOULD, TJ ;

BALESTRA, M ;

WITTMAN, MD ;

GARY, JA ;

ROSSANO, LT ;

KALLMERTEN, J .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (17) :3889-3901

[18]

GRAMATICA P, 1986, TETRAHEDRON, V24, P6687

[19] ACYCLIC STEREOSELECTION .15. SEQUENTIAL ALDOL-CLAISEN AS A METHOD FOR 1,5-STEREOSELECTION - TOTAL SYNTHESIS OF THE VITAMIN-E SIDE-CHAIN [J].

HEATHCOCK, CH ;

JARVI, ET .

TETRAHEDRON LETTERS, 1982, 23 (28) :2825-2828

[20] NEW EFFICIENT METHODS FOR THE SYNTHESIS AND INSITU PREPARATION OF RUTHENIUM(II) COMPLEXES OF ATROPISOMERIC DIPHOSPHINES AND THEIR APPLICATION IN ASYMMETRIC CATALYTIC HYDROGENATIONS [J].

HEISER, B ;

BROGER, EA ;

CRAMERI, Y .

TETRAHEDRON-ASYMMETRY, 1991, 2 (01) :51-62

← 1 2 3 4 5 →