A STRAIGHTFORWARD SYNTHESIS OF (-)-(1S,2R)-ALLONORCORONAMIC ACID USING D-MANNITOL AS THE CHIRAL SOURCE

被引：21

作者：

CATIVIELA, C

DIAZDEVILLEGAS, MD

JIMENEZ, AI

机构：

[1] Departamento de Química Orgánica. Instituto de Ciencia de Materiales

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 08期

关键词：

D O I：

10.1016/0957-4166(95)00269-U

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(-)-(1S,2R)-Allonorcoronamic acid was synthesized in its enantiomerically pure form from methyl (1S,2R)-1-benzamido-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclopropanecarboxylate, which is easily obtained by methylene insertion on the chiral azlactone derived from 1,2-O-isopropylidene-D-glyceraldehyde.

引用

收藏

页码：2067 / 2072

页数：6

相关论文

共 33 条

[1] ETHYLENE BIOSYNTHESIS - IDENTIFICATION OF 1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID AS AN INTERMEDIATE IN THE CONVERSION OF METHIONINE TO ETHYLENE [J].

ADAMS, DO ;

YANG, SF .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1979, 76 (01) :170-174

[2] INHIBITION OF PIG-KIDNEY L-AROMATIC AMINO-ACID DECARBOXYLASE BY 2,3-METHANO-META-TYROSINES [J].

AHMAD, S ;

PHILLIPS, RS ;

STAMMER, CH .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (08) :1410-1417

[3]

ALAMI A, 1993, B SOC CHIM FR, V130, P5

[4] THE RESOLUTION OF RACEMIC 2-ALKYL-1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACIDS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

RAWLINGS, BJ ;

JONES, RH .

TETRAHEDRON LETTERS, 1985, 26 (04) :485-488

[5] ENZYME-INHIBITION BY ELECTROPHILIC CYCLOPROPANE DERIVATIVES [J].

BRECKENRIDGE, RJ ;

SUCKLING, CJ .

TETRAHEDRON, 1986, 42 (20) :5665-5677

[6]

BURGESS K, 1994, SYNLETT, P575

[7] A GAMMA-TURN STRUCTURE INDUCED BY 2S,3S-2,3-METHANOMETHIONINE [J].

BURGESS, K ;

HO, KK ;

PETTITT, BM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :799-800

[8] I-AMINOCYCLOPROPANE-I-CARBOXYLIC ACID - NEW AMINO-ACID IN PERRY PEARS AND CIDER APPLES [J].

BURROUGHS, LF .

NATURE, 1957, 179 (4555) :360-361

[9] DIASTEREOSELECTIVE SYNTHESIS OF CYCLOPROPYL PHENYLALANINES AND THEIR INCORPORATION INTO DIPEPTIDES [J].

CAMPBELL, MM ;

HORWELL, DC ;

MAHON, MF ;

PRITCHARD, MC ;

WALFORD, SP .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (04) :667-670

[10] A SIMPLE SYNTHESIS OF (-)-(1S,2R)-ALLOCORONAMIC ACID IN ITS ENANTIOMERICALLY PURE FORM [J].

CATIVIELA, C ;

DIAZDEVILLEGAS, MD ;

JIMENEZ, AI .

TETRAHEDRON-ASYMMETRY, 1995, 6 (01) :177-182

← 1 2 3 4 →