Synthesis of the Bacterial Coenzyme Methoxatin

Article abstract of DOI:10.1021/jo00136a002

The details of a total synthesis of methoxatin (1), the coenzyme of several bacterial alcohol dehydrogenases, are presented.Methoxatin has been prepared in 13 steps by starting from 2,3-dimethoxytoluene.The successful synthetic strategy for construction of the coenzyme used a Pfitzinger synthesis for preparation of the quinoline dicarboxylic acid portion of 1 and an "umpolung" variation of the Reissert indole synthesis for annulation of the remaining pyrrole ring.