Total Synthesis of the Antitumor Antibiotic Streptonigrin

Steven M. Weinreb; Fatima Z. Basha; Satoshi Hibino; Nazir A. Khatri; Deukjoon Kim; Walter E. Pye; Tai Teh Wu

doi:10.1021/ja00366a028

Total Synthesis of the Antitumor Antibiotic Streptonigrin

Steven M. Weinreb
, Fatima Z. Basha
, Satoshi Hibino
, Nazir A. Khatri
, Deukjoon Kim
, Walter E. Pye
, Tai Teh Wu

Chemistry

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

86 Scopus citations

Abstract

Full details of the previously reported total synthesis of streptonigrin (1) are presented. The successful synthetic strategy outlined in Scheme I involves use of an imino Diels-Alder cycloaddition for construction of the pyridine C ring of 1 and a modified Friedlander synthesis for annulation of the AB quinoline quinone ring system.

Original language	English (US)
Pages (from-to)	536-544
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	104
Issue number	2
DOIs	https://doi.org/10.1021/ja00366a028
State	Published - 1982

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja00366a028

Cite this

@article{14daee17055747c2bea0efd775a5a47f,

title = "Total Synthesis of the Antitumor Antibiotic Streptonigrin",

abstract = "Full details of the previously reported total synthesis of streptonigrin (1) are presented. The successful synthetic strategy outlined in Scheme I involves use of an imino Diels-Alder cycloaddition for construction of the pyridine C ring of 1 and a modified Friedlander synthesis for annulation of the AB quinoline quinone ring system.",

author = "Weinreb, \{Steven M.\} and Basha, \{Fatima Z.\} and Satoshi Hibino and Khatri, \{Nazir A.\} and Deukjoon Kim and Pye, \{Walter E.\} and Wu, \{Tai Teh\}",

year = "1982",

doi = "10.1021/ja00366a028",

language = "English (US)",

volume = "104",

pages = "536--544",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "2",

}

TY - JOUR

T1 - Total Synthesis of the Antitumor Antibiotic Streptonigrin

AU - Weinreb, Steven M.

AU - Basha, Fatima Z.

AU - Hibino, Satoshi

AU - Khatri, Nazir A.

AU - Kim, Deukjoon

AU - Pye, Walter E.

AU - Wu, Tai Teh

PY - 1982

Y1 - 1982

N2 - Full details of the previously reported total synthesis of streptonigrin (1) are presented. The successful synthetic strategy outlined in Scheme I involves use of an imino Diels-Alder cycloaddition for construction of the pyridine C ring of 1 and a modified Friedlander synthesis for annulation of the AB quinoline quinone ring system.

AB - Full details of the previously reported total synthesis of streptonigrin (1) are presented. The successful synthetic strategy outlined in Scheme I involves use of an imino Diels-Alder cycloaddition for construction of the pyridine C ring of 1 and a modified Friedlander synthesis for annulation of the AB quinoline quinone ring system.

UR - https://www.scopus.com/pages/publications/0020053088

UR - https://www.scopus.com/pages/publications/0020053088#tab=citedBy

U2 - 10.1021/ja00366a028

DO - 10.1021/ja00366a028

M3 - Article

AN - SCOPUS:0020053088

SN - 0002-7863

VL - 104

SP - 536

EP - 544

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 2

ER -

Total Synthesis of the Antitumor Antibiotic Streptonigrin

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this