A new and efficient total synthesis of streptonigrin

Kende, Andrew S.; Lorah, Dennis P.; Boatman, Rodney J.

doi:10.1021/ja00395a071

Cited by 50 publications

(18 citation statements)

References 4 publications

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“…Despite the large number of natural and synthetic active derivatives, only a few of them have qualified for clinical trials [7,8,9,10]. The most important problem in this class of compounds is due to their toxicity.…”

Section: Discussionmentioning

confidence: 99%

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5,8-Quinolinedione Scaffold as a Promising Moiety of Bioactive Agents

et al. 2019

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Natural 5,8-quinolinedione antibiotics exhibit a broad spectrum of activities including anticancer, antibacterial, antifungal, and antimalarial activities. The structure–activity research showed that the 5,8-quinolinedione scaffold is responsible for its biological effect. The subject of this review report is a presentation of the pharmacological activity of synthetic 5,8-quinolinedione compounds containing different groups at C-6 and/or C-7 positions. The relationship between the activity and the mechanism of action is included if these data have been included in the original literature. The review mostly covers the period between 2000 and 2019. Previously published literature data were used to present historical points.

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Section: Discussionmentioning

confidence: 99%

“…Finally, the structure of compound 1 was confirmed by x-ray crystallography in 1975 [6]. The total synthesis of the alkaloid 1 has been carried out by two research groups (Weinreb et al and Kende et al) from 1980 to 1982 [7,8].…”

Section: Introductionmentioning

confidence: 99%

5,8-Quinolinedione Scaffold as a Promising Moiety of Bioactive Agents

et al. 2019

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“…The antitumor antibiotic streptonigrin ( 84 ) was synthesized in an efficient manner by Kende and co-workers, where one of the amine groups was introduced by the Yamada modification of the Curtius rearrangement. 86 Similarly, in the synthesis of streptonigrone ( 87 ) by Boger and co-workers, the pyridine C5 amine was introduced by the Shioiri-Yamada modification of the Curtius rearrangement. 87 In this case, the intermediate isocyanate was found to be very stable.…”

Section: Application Of the Curtius Rearrangement In Total Synthesismentioning

confidence: 99%

The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses

2018

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The Curtius rearrangement is a versatile reaction in which a carboxylic acid can be converted to an isocyanate through an acyl azide intermediate under mild conditions. The resulting stable isocyanate can then be readily transformed into a variety of amines and amine derivatives including urethanes and ureas. There have been wide-ranging applications of the Curtius rearrangement in the synthesis of natural products and their derivatives. Also, this reaction has been extensively utilized in the synthesis and application of a variety of biomolecules. In this review, we present mechanistic studies, chemical methodologies and reagents for the synthesis of isocyanates from carboxylic acids, the conversion of isocyanates to amines and amine derivatives, and their applications in the synthesis of bioactive natural products and their congeners.

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“…The basic strategy developed by Kende and co-workers 55,108,109 was to concentrate on the regiocontrolled synthesis of the CD-ring portion and then utilize a Friedländer synthesis for the attachment of the AB-ring system (see Scheme 25a or Scheme 25b). The known ketoenamine intermediate 63, as prepared earlier by Liao,…”

Section: Kende's Approachmentioning

confidence: 99%