Synthesis of the Bacterial Coenzyme Methoxatin

James A. Gainor, Steven M. Weinreb

Research output: Contribution to journalArticlepeer-review

45 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2833-2837
Number of pages5
JournalJournal of Organic Chemistry
Volume47
Issue number15
DOIs
StatePublished - 1982

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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