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.
All Science Journal Classification (ASJC) codes
- Organic Chemistry