Enantioselective synthesis of (R)-(-)-mevalonolactone via cyclic sulfate methodology

被引：34

作者：

Fernandes, RA ^{[1
]}

Kumar, P ^{[1
]}

机构：

[1] Natl Chem Lab, Div Organ Chem Technol, Poona 411008, Maharashtra, India

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 22期

关键词：

D O I：

10.1016/S0957-4166(99)00496-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An asymmetric synthesis of (R)-(-)-mevalonolactone is described using the Sharpless asymmetric dihydroxylation and the regioselective nucleophilic opening of a cyclic sulfate as key steps. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4349 / 4356

页数：8

共 46 条

[1]

ABUSHANAB E, 1978, TETRAHEDRON LETT, P3415

[2] A new ligand class for the asymmetric dihydroxylation of olefins [J].

Becker, H ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (04) :448-451

[3] SYNTHESIS OF (S)-(+)-MEVALONOLACTONE AND MEVALONATE ANALOGS [J].

BOLITT, V ;

MIOSKOWSKI, C ;

BHATT, RK ;

FALCK, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) :4238-4240

[4] 1ST PRACTICAL ASYMMETRIC-SYNTHESIS OF R-(-)-AND S-(+)-MEVALONOLACTONES FROM A SINGLE ACHIRAL PRECURSOR [J].

BONADIES, F ;

ROSSI, G ;

BONINI, C .

TETRAHEDRON LETTERS, 1984, 25 (47) :5431-5434

[5] USE OF PYRIDINIUM CHLOROCHROMATE AS METHYLENE OXIDANT IN 5,6-DIHYDROPYRANS - A PRACTICAL, ONE-STEP PREPARATION OF THE ANHYDROMEVALONOLACTONE [J].

BONADIES, F ;

DIFABIO, R ;

BONINI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1647-1649

[6] THE MODE OF INCORPORATION OF C-2 HYDROGEN-ATOMS OF MEVALONIC ACID INTO PROTOSTEROLS AND STEROLS [J].

CASPI, E .

TETRAHEDRON, 1986, 42 (01) :3-50

[7] HIGHLY ENANTIOSELECTIVE AND REGIOSELECTIVE CATALYTIC DIHYDROXYLATION OF HOMOALLYLIC ALCOHOL DERIVATIVES [J].

COREY, EJ ;

GUZMANPEREZ, A ;

NOE, MC .

TETRAHEDRON LETTERS, 1995, 36 (20) :3481-3484

[8] PREPARATION OF R- AND S-MEVALONOLACTONES [J].

CORNFORTH, RH ;

POPJAK, G ;

CORNFORTH, JW .

TETRAHEDRON, 1962, 18 (DEC) :1351-&

[9] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[10] ENANTIOSELECTIVE SYNTHESIS OF 2-METHYL-2-HYDROXY-GAMMA-BUTYROLACTONE AND ITS APPLICATION IN THE ASYMMETRIC-SYNTHESIS OF FRONTALIN AND MEVALONOLACTONE [J].

DAVIS, FA ;

REDDY, GV ;

CHEN, BC ;

KUMAR, A ;

HAQUE, MS .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6148-6153

← 1 2 3 4 5 →