ENZYMATIC RESOLUTION OF A KEY STEREOCHEMICAL INTERMEDIATE FOR THE SYNTHESIS OF (-)-TAXOL

被引：28

作者：

JOHNSON, CR

XU, YP

NICOLAOU, KC

YANG, Z

GUY, RK

DONG, JG

BEROVA, N

机构：

[1] Scripps Res Inst, DEPT CHEM, LA JOLLA, CA 92037 USA

[2] UNIV CALIF SAN DIEGO, DEPT CHEM & BIOCHEM, LA JOLLA, CA 92093 USA

[3] COLUMBIA UNIV, DEPT CHEM, NEW YORK, NY 10027 USA

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 19期

关键词：

D O I：

10.1016/0040-4039(95)00523-F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The taxol intermediate, racemic 3, was subjected to two consecutive kinetic resolutions with recombinant Candida antarctica lipase Bin isopropenyl acetate/hexane. The absolute stereochemistry of the resulting acetate (+)-5 of > 99% enantiopurity, was assigned based on NMR and CD methods.

引用

页码：3291 / 3294

页数：4

共 29 条

[1] SYNTHETIC STUDIES ON C-19 OXYGENATED PREGNANES
BAGLI, JF
MORAND, PF
GAUDRY, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (05) : 1207 - &
[2] LIPASE ASYMMETRIZATION OF CIS-3,7-DIHYDROXYCYCLOHEPTENE DERIVATIVES IN ORGANIC AND AQUEOUS-MEDIA
BIS, SJ
WHITAKER, DT
JOHNSON, CR
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (05) : 875 - 878
[3] BRIEVA R, 1991, J CHEM SOC CHEM COMM, P1386
[4] AMPLIFICATION OF ENANTIOSELECTIVITY IN BIOCATALYZED KINETIC RESOLUTION OF RACEMIC ALCOHOLS
CHEN, CS
LIU, YC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) : 1966 - 1968
[5] ASYMMETRIC-SYNTHESIS - METAL-COMPLEX MEDIATED SYNTHESIS OF CHIRAL GLYCINE BY ENANTIOSELECTIVE PROTON-EXCHANGE
DOKUZOVIC, Z
ROBERTS, NK
SAWYER, JF
WHELAN, J
BOSNICH, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) : 2034 - 2039
[6] ENZYME-CATALYZED ASYMMETRIZATION OF BIS(HYDROXYMETHYL)-TETRAHYDROFURANS
ESTERMANN, H
PRASAD, K
SHAPIRO, MJ
REPIC, O
HARDTMANN, GE
BOLSTERLI, JJ
WALKINSHAW, MD
[J]. TETRAHEDRON LETTERS, 1990, 31 (04) : 445 - 448
[7] ENZYMATIC RESOLUTION OF 2-SUBSTITUTED OXIRANEMETHANOLS, A CLASS OF SYNTHETICALLY USEFUL BUILDING-BLOCKS BEARING A CHIRAL QUATERNARY CENTER
FERRABOSCHI, P
BREMBILLA, D
GRISENTI, P
SANTANIELLO, E
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) : 5478 - 5480
[8] HIGHLY DIASTEREOSELECTIVE INTERESTERIFICATION REACTIONS INVOLVING A RACEMIC ACETATE AND A RACEMIC CARBOXYLIC-ACID CATALYZED BY LIPASE ENZYMES
FOWLER, PW
MACFARLANE, ELA
ROBERTS, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (07) : 453 - 455
[9] TAXOL AND TAXOTERE - DISCOVERY, CHEMISTRY, AND STRUCTURE-ACTIVITY-RELATIONSHIPS
GUENARD, D
GUERITTEVOEGELEIN, F
POTIER, P
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (04) : 160 - 167
[10] GUENARD D, 1992, TETRAHEDRON, V48

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