Synthesis of the Bacterial Coenzyme Methoxatin

James A. Gainor; Steven M. Weinreb

doi:10.1021/jo00136a002

Synthesis of the Bacterial Coenzyme Methoxatin

James A. Gainor, Steven M. Weinreb

Chemistry

Research output: Contribution to journal › Article › peer-review

48 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 language	English (US)
Pages (from-to)	2833-2837
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	47
Issue number	15
DOIs	https://doi.org/10.1021/jo00136a002
State	Published - 1982

All Science Journal Classification (ASJC) codes

Organic Chemistry

Access to Document

10.1021/jo00136a002

Cite this

@article{6a0bfd9d7ebb4e99806c1cf73b7fcc9d,

title = "Synthesis of the Bacterial Coenzyme Methoxatin",

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.",

author = "Gainor, {James A.} and Weinreb, {Steven M.}",

year = "1982",

doi = "10.1021/jo00136a002",

language = "English (US)",

volume = "47",

pages = "2833--2837",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Synthesis of the Bacterial Coenzyme Methoxatin

AU - Gainor, James A.

AU - Weinreb, Steven M.

PY - 1982

Y1 - 1982

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0042277504&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0042277504&partnerID=8YFLogxK

U2 - 10.1021/jo00136a002

DO - 10.1021/jo00136a002

M3 - Article

AN - SCOPUS:0042277504

SN - 0022-3263

VL - 47

SP - 2833

EP - 2837

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 15

ER -

Synthesis of the Bacterial Coenzyme Methoxatin

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this