Concise syntheses of acromelic acid A and allo-acromelic acid A

被引：21

作者：

Baldwin, JE ^{[1
]}

Fryer, AM ^{[1
]}

Pritchard, GJ ^{[1
]}

Spyvee, MR ^{[1
]}

Whitehead, RC ^{[1
]}

Wood, ME ^{[1
]}

机构：

[1] Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(97)10641-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acromelic acid A 1 and allo-acromelic acid A 12 were synthesised in a biomimetic fashion. An oxidative cleavage - recyclisation strategy was used to construct the requisite C-4 pyridone from an intermediate catechol. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：707 / 710

页数：4

相关论文

共 21 条

[1] Towards a versatile synthesis of kainoids .1. Introduction of the C-3 and C-4 substituents [J].

Baldwin, JE ;

Bamford, SJ ;

Fryer, AM ;

Rudolph, MPW ;

Wood, ME .

TETRAHEDRON, 1997, 53 (14) :5233-5254

[2] A biomimetic synthesis of stizolobinic acid [J].

Baldwin, JE ;

Spyvee, MR ;

Whitehead, RC .

TETRAHEDRON LETTERS, 1997, 38 (15) :2771-2774

[3] Stereocontrol in the synthesis of kainoids [J].

Baldwin, JE ;

Fryer, AM ;

Spyvee, MR ;

Whitehead, RC ;

Wood, ME .

TETRAHEDRON LETTERS, 1996, 37 (38) :6923-6924

[4] BIOMIMETIC SYNTHESES OF STIZOLOBIC ACID AND 3-(6-CARBOXY-2-OXO-4-PYRIDYL)ALANINE [J].

BALDWIN, JE ;

SPYVEE, MR ;

WHITEHEAD, RC .

TETRAHEDRON LETTERS, 1994, 35 (35) :6575-6576

[5] Towards a versatile synthesis of kainoids .3. Efficient methods for control of C-4 stereochemistry [J].

Baldwin, JE ;

Fryer, AM ;

Spyvee, MR ;

Whitehead, RC ;

Wood, ME .

TETRAHEDRON, 1997, 53 (14) :5273-5290

[6]

BALDWIN JE, 1995, TETRAHEDRON LETT, V36, P4869

[7]

BALOGH V, 1971, J ORG CHEM, V36, P1339

[8] DOPA RING-CLEAVAGE IN BIOGENESIS OF STIZOLOBIC ACID IN MUCUNA-DEERINGIANA [J].

ELLIS, BE .

PHYTOCHEMISTRY, 1976, 15 (04) :489-491

[9] SYNTHESIS OF SIMPLE DERIVATIVES OF "(2Z,4Z)-3-METHYL-2,4-HEXADIENEDIOIC ACID [J].

JAROSZEWSKI, JW ;

ETTLINGER, MG .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1212-1215

[10] ACROMELIC ACID-A AND ACID-B - POTENT NEUROEXCITATORY AMINO-ACIDS ISOLATED FROM CLITOCYBE-ACROMELALGA [J].

KONNO, K ;

HASHIMOTO, K ;

OHFUNE, Y ;

SHIRAHAMA, H ;

MATSUMOTO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4807-4815