Tetrahedron

Synthesis of the bacterial coenzyme methoxatin

AR Mackenzie, CJ Moody, CW Rees

Index: MacKenzie, A. Roderick; Moody, Christopher J.; Rees, Charles W. Tetrahedron, 1986 , vol. 42, # 12 p. 3259 - 3268

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Citation Number: 80

Abstract

A short total synthesis of the bacterial coenzyme methoxatin (1)(4, 5-dihydro-4, 5-dioxo-1H- pyrrolo [2, 3-f] quinoline-2, 7, 9-tricarboxylic acid) is described. The route involves the two step conversion of 4-acetamido-2-benzy1oxybenzaldehyde (5b) into methyl 6-acctamido-4- benzyloxyindole-2-carboxylate (7b)(74%), followed by regioselective annulation of the third ring (55%), and debenzylation and oxidation with benzoyl t-butyl nitroxide to give the ...

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