(R)-(+)-5-ETHYL-5-METHYL-1,3-DIOXOLANE-2,4-DIONE AND (S)-(-)-5-ETHYL-5-METHYL-1,3-DIOXOLANE-2,4-DIONE REAGENTS FOR THE DIRECT PREPARATION OF ALPHA-HYDROXY-ALPHA-METHYLBUTYRATE ESTERS - ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF THE ALPHA-ACETOXY-ALPHA-METHYLBUTYRATE ESTER SIDE-CHAIN OF QUASSIMARIN VIA TOTAL SYNTHESIS

被引：29

作者：

MOHER, ED ^{[1
]}

GRIECO, PA ^{[1
]}

COLLINS, JL ^{[1
]}

机构：

[1] INDIANA UNIV, DEPT CHEM, BLOOMINGTON, IN 47405 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 15期

关键词：

D O I：

10.1021/jo00067a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The preparation and use of (R)-(+)- and (S)-(-)-5-ethyl-5-methyl-1,3-dioxolane-2,4-diones for the direct preparation of chiral alpha-hydroxy-alpha-methylbutyrate esters are described.

引用

页码：3789 / 3790

页数：2

共 32 条

[1] GENERAL-SYNTHESIS OF PENTACYCLIC QUASSINOIDS [J].

BATT, DG ;

TAKAMURA, N ;

GANEM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (11) :3353-3354

[2] SYNTHESIS OF A MODEL FOR THE BCE RING-SYSTEM OF BRUCEANTIN - CAVEAT ON THE CYCLOHEXENE -] TRANS DIAXIAL DIOL CONVERSION [J].

DAILEY, OD ;

FUCHS, PL .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (02) :216-236

[3] A DELTA-LACTONE SYNTHESIS INVOLVING AN INTRAMOLECULAR 1,4-ADDITION OF ALPHA-IODOACETATES TO ENONES [J].

DEMIR, AS ;

GROSS, RS ;

DUNLAP, NK ;

BASHIRHASHEMI, A ;

WATT, DS .

TETRAHEDRON LETTERS, 1986, 27 (46) :5567-5570

[4]

GAUDEMER ALAIN, 1965, PHYTOCHEMISTRY, V4, P149, DOI 10.1016/S0031-9422(00)86157-9

[5] SYNTHETIC STUDIES ON QUASSIMARIN - CONSTRUCTION OF THE PENTACYCLIC CARBON SKELETON [J].

GRIECO, PA ;

INANAGA, J ;

SHAM, HL ;

SASAKI, S ;

KIM, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (13) :1044-1046

[6] SYNTHETIC STUDIES ON QUASSINOIDS - CONSTRUCTION OF THE BCE RING-SYSTEM OF QUASSIMARIN AND RELATED NATURAL-PRODUCTS [J].

GRIECO, PA ;

SHAM, HL ;

INANAGA, J ;

KIM, HB ;

TUTHILL, PA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (20) :1345-1347

[7] CHEMICAL-TRANSFORMATIONS IN THE QUASSINOID SERIES - NOVEL COPPER(II)-MEDIATED RING CONTRACTION OF DELTA-LACTONES TO GAMMA-LACTONES - A SYNTHETIC ENTRY INTO THE SAMADERINS [J].

INANAGA, J ;

SASAKI, S ;

GRIECO, PA ;

KIM, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (16) :4800-4802

[8] ASYMMETRIC HALOLACTONIZATION REACTION .1. ASYMMETRIC SYNTHESIS OF OPTICALLY-ACTIVE ALPHA,ALPHA-DISUBSTITUTED-ALPHA-HYDROXY ACIDS FROM ALPHA,BETA-UNSATURATED ACIDS BY THE NOVEL USE OF HALOLACTONIZATION REACTION [J].

JEW, S ;

TERASHIMA, S ;

KOGA, K .

TETRAHEDRON, 1979, 35 (20) :2337-2343

[9] SYNTHETIC STUDIES ON QUASSINOIDS - A NOVEL, GENERAL-METHOD FOR THE ELABORATION OF THE C(8),C(13) EPOXYMETHANO BRIDGE OF QUASSIMARIN [J].

KANAI, K ;

ZELLE, RE ;

SHAM, HL ;

GRIECO, PA ;

CALLANT, P .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (20) :3867-3868

[10] MODEL STUDIES IN THE QUASSIMARIN SERIES - TOTAL SYNTHESIS OF DE-A-QUASSIMARIN [J].

KAWABATA, T ;

GRIECO, PA ;

SHAM, HL ;

KIM, HB ;

JAW, JY ;

TU, SZ .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (15) :3346-3354

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