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

85 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

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10.1021/ja00366a028

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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",

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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.

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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

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