Synthetic studies on kinamycin antibiotics: elaboration of a highly oxygenated D-ring

Kumamoto, Takuya; Tabe, Nobutaka; Yamaguchi, Kentaro; Ishikawa, Tsutomu

doi:10.1016/s0040-4039(00)00932-1

Cited by 16 publications

(4 citation statements)

References 15 publications

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“…A year after the disclosure of Porco's synthesis, Kumamoto and co-workers published their total synthesis of racemic methyl kinamycin C, 89 a synthetic derivative of the natural product reported by Omura et al during the structural determination of kinamycin C. 76 Their approach relied on the construction of the highly oxygenated cyclohexane ring of the natural product by a Diels-Alder reaction, followed by further elaboration (Scheme 15). [90][91][92] This approach is different from the majority of disconnections used in the synthesis of the diazobenzofluorene ring system, which generally disconnect through the central fluorene ring (Nicolaou, Porco and Herzon q.v. ), or the quinone (Hauser, 93 Shairq.v.).…”

Section: Synthesismentioning

confidence: 99%

Natural products containing a diazo group

Nawrat

Moody

2011

Nat. Prod. Rep.

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Although diazo compounds are probably best known for their involvement as versatile intermediates in modern synthetic organic chemistry, a small number of such compounds also occur naturally. Many of the early examples, such as azaserine, originally isolated in the 1950s, have antitumour properties and consist of modified α-amino acids. More recently, other more complex diazo compounds have been isolated from natural sources, and these include diazobenzoquinones, diazonaphthoquinones, such as the SF2415 and A80915 antibiotics, and the diazofluorene-based kinamycins and lomaiviticins. This report will cover the isolation, biosynthesis, biological activity and synthesis of natural products containing a diazo group.

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Section: Synthesismentioning

confidence: 99%

Natural products containing a diazo group

Nawrat

Moody

2011

Nat. Prod. Rep.

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“…[5] In the synthesis of the tetracyclic core of benzo[b]fluorenes, which are prominently featured in some natural compounds exhibiting interesting biological activity, we prepared different dihydronaphthalenes as their immediate precursors. In recent years, synthetic efforts in this area have resulted in the synthesis of natural [6] and non-natural benzo[b]fluorenes. [7] Some of these derivatives have been used in the study of cationic intermediates [8] or were found to be promising compounds for the construction of organic light-emitting diodes.…”

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confidence: 99%

Fast Synthesis of Benzofluorenes by Selenium‐Mediated Carbocyclizations

Shahzad

Wirth

2009

Angew Chem Int Ed

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“…In letzter Zeit haben Untersuchungen in dieser Richtung zur Synthese von Benzo[b]fluoren-Systemen geführt, [6] die auch in Naturstoffen anzutreffen sind. [7] Einige dieser Derivate wurden sogar zum Studium kationischer Intermediate eingesetzt [8] oder sind vielversprechende Verbindungen zur Konstruktion organischer Leuchtdioden. [9] Intramolekulare [4+2]-Cycloadditionen von 2-Propinyldiarylacetylenen [10] oder die radikalische Cycloaromatisierung nichtkonjugierter Benzotriine [11] können zur Synthese von Benzo[b]fluorenen verwendet werden.…”

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