SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY LACTONES BY SHARPLESS ASYMMETRIC DIHYDROXYLATIONS OF KETENE ACETALS, ENOL ETHERS, AND ENE LACTONES

被引：37

作者：

CURRAN, DP

KO, SB

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 21期

关键词：

D O I：

10.1021/jo00100a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three different AD routes to optically active alpha-hydroxy lactones of good to excellent optical purity are reported. The substrates for the AD reaction are endocyclic ketene acetals, endocyclic enol ethers, and exocyclic alpha,beta-unsaturated lactones.

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页码：6139 / 6141

页数：3

相关论文

共 22 条

[1] SYNTHESES AND CRYSTAL-STRUCTURES OF THE CINCHONA ALKALOID DERIVATIVES USED AS LIGANDS IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS [J].

AMBERG, W ;

BENNANI, YL ;

CHADHA, RK ;

CRISPINO, GA ;

DAVIS, WD ;

HARTUNG, J ;

JEONG, KS ;

OGINO, Y ;

SHIBATA, T ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :844-849

[2] A DRAMATIC LIGAND EFFECT ON THE RELATIVE REACTIVITIES OF SUBSTITUTED ALKENES WITH OSMIUM-TETROXIDE [J].

ANDERSSON, PG ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7047-7048

[3] AN EFFICIENT STEREOSELECTIVE SYNTHESIS OF DELTA-4,5-PIPECOLIC ESTERS [J].

ANGLE, SR ;

BREITENBUCHER, JG ;

ARNAIZ, DO .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5947-5955

[4] ASYMMETRIC DIHYDROXYLATION (AD) OF N,N-DIALKYL AND N-METHOXY-N-METHYL ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED AMIDES [J].

BENNANI, YL ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1993, 34 (13) :2079-2082

[5] A 10-STEP, ASYMMETRIC-SYNTHESIS OF (S)-CAMPTOTHECIN [J].

COMINS, DL ;

BAEVSKY, MF ;

HONG, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10971-10972

[6] TOTAL SYNTHESIS OF GINKGOLIDE-A [J].

COREY, EJ ;

GHOSH, AK .

TETRAHEDRON LETTERS, 1988, 29 (26) :3205-3206

[7] TOPOISOMERASE-I INHIBITORS - TOPOTECAN AND IRENOTECAN [J].

CREEMERS, GJ ;

LUND, B ;

VERWEIJ, J .

CANCER TREATMENT REVIEWS, 1994, 20 (01) :73-96

[8] IMPROVED ENANTIOSELECTIVITY IN ASYMMETRIC DIHYDROXYLATIONS OF TERMINAL OLEFINS USING PYRIMIDINE LIGANDS [J].

CRISPINO, GA ;

JEONG, KS ;

KOLB, HC ;

WANG, ZM ;

XU, DQ ;

SHARPLESS, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) :3785-3786

[9]

CURRAN DP, 1993, J CHIN CHEM SOC-TAIP, V40, P1

[10] NEW 4+1 RADICAL ANNULATIONS - A FORMAL TOTAL SYNTHESIS OF (+/-)-CAMPTOTHECIN [J].

CURRAN, DP ;

LIU, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5863-5864