(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

[21] SYNTHETIC STUDIES ON QUASSINOIDS - TOTAL SYNTHESIS OF SIMALIKALACTONE-D AND ASSIGNMENT OF THE ABSOLUTE-CONFIGURATION OF THE ALPHA-METHYLBUTYRATE ESTER SIDE-CHAIN [J].

MOHER, ED ;

COLLINS, JL ;

GRIECO, PA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2764-2765

[22]

NYBURG SC, 1965, J CHEM SOC CHEM COMM, P203

[23]

Polonsky J, 1985, Fortschr Chem Org Naturst, V47, P221

[24] SYNTHETIC STUDIES TOWARD QUASSINOIDS - ANOMALOUS RESULTS FROM THE METAL-AMMONIA REDUCTION OF PHENANTHRENONE DERIVATIVES [J].

SASAKI, S ;

GRIECO, PA ;

HUFFMAN, JC ;

CALLANT, P ;

IMAMURA, PM .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24) :4880-4884

[25] AN APPROACH TO QUASSIMARIN BASED ON AN EXO-SELECTIVE INTRAMOLECULAR DIELS-ALDER REACTION [J].

SCHLESSINGER, RH ;

WONG, JW ;

POSS, MA ;

SPRINGER, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3950-3951

[26] SYNTHETIC STUDIES TOWARD ANTITUMOR QUASSINOIDS .2. A CHIRAL APPROACH TO QUASSIMARIN VIA INTRAMOLECULAR DIELS-ALDER REACTION [J].

SHISHIDO, K ;

TAKAHASHI, K ;

OSHIO, Y ;

FUKUMOTO, K ;

KAMETANI, T ;

HONDA, T .

TETRAHEDRON LETTERS, 1986, 27 (12) :1339-1342

[27] A SYNTHETIC APPROACH TO (-)-QUASSIMARIN BASED ON INTRAMOLECULAR DIELS-ALDER STRATEGY [J].

SHISHIDO, K ;

TAKAHASHI, K ;

FUKUMOTO, K ;

KAMETANI, T ;

HONDA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (26) :5704-5714

[28]

SHISHIDO K, 1988, HETEROCYCLES, V27, P495

[29] CHEMICAL-TRANSFORMATIONS IN THE QUASSINOID SERIES - CONSTRUCTION OF THE SENSITIVE HYDROXY ENONE FUNCTIONALITY PRESENT IN RING A OF QUASSIMARIN AND RELATED QUASSINOIDS [J].

SPOHN, RF ;

GRIECO, PA ;

NARGUND, RP .

TETRAHEDRON LETTERS, 1987, 28 (22) :2491-2494

[30]

STEWART J, 1991, GRADUATE FELLOW

← 1 2 3 4 →