One-pot multistep Bohlmann-Rahtz heteroannulation reactions: Synthesis of dimethyl sulfomycinamate

被引：78

作者：

Bagley, MC

Chapaneri, K

Dale, JW

Xiong, X

Bower, J

机构：

[1] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales

[2] Vernalis, Cambridge CB1 6GB, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 04期

关键词：

D O I：

10.1021/jo048106q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.

引用

收藏

页码：1389 / 1399

页数：11

相关论文

共 80 条

[1] THE STRUCTURES OF SULFOMYCIN-I AND BERNINAMYCIN-A [J].

ABE, H ;

KUSHIDA, K ;

SHIOBARA, Y ;

KODAMA, M .

TETRAHEDRON LETTERS, 1988, 29 (12) :1401-1404

[2] Practical routes to diacetylenic ketones and their application for the preparation of alkynyl substituted pyridines, pyrimidines and pyrazoles [J].

Adamo, MFA ;

Adlington, RM ;

Baldwin, JE ;

Pritchard, GJ ;

Rathmell, RE .

TETRAHEDRON, 2003, 59 (13) :2197-2205

[3] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones as reactive substrates [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ ;

Tang, LT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15) :2311-2316

[4] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ ;

Tang, LT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03) :303-305

[5] Thiopeptide antibiotics [J].

Bagley, MC ;

Dale, JW ;

Merritt, EA ;

Xiong, A .

CHEMICAL REVIEWS, 2005, 105 (02) :685-714

[6] Stereoselective synthesis of the γ-lactam hydrolysate of the thiopeptide cyclothiazomycin [J].

Bagley, MC ;

Xiong, X .

ORGANIC LETTERS, 2004, 6 (19) :3401-3404

[7] First synthesis of an amythiamicin pyridine cluster [J].

Bagley, MC ;

Dale, JW ;

Jenkins, RL ;

Bower, J .

CHEMICAL COMMUNICATIONS, 2004, (01) :102-103

[8] A facile solution phase combinatorial synthesis of tetrasubstituted pyridines using the Bohlmann-Rahtz heteroannulation reaction [J].

Bagley, MC ;

Dale, JW ;

Ohnesorge, M ;

Xiong, X ;

Bower, J .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (01) :41-44

[9] Synthesis of dimethyl sulfomycinamate [J].

Bagley, MC ;

Dale, JW ;

Xiong, X ;

Bower, J .

ORGANIC LETTERS, 2003, 5 (23) :4421-4424

[10] A new one-step synthesis of pyridines under microwave-assisted conditions [J].

Bagley, MC ;

Lunn, R ;

Xiong, X .

TETRAHEDRON LETTERS, 2002, 43 (46) :8331-8334

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