Total Synthesis of γ‑Indomycinone and Kidamycinone by Means of Two Regioselective Diels–Alder Reactions

Total Synthesis of γ‑Indomycinone and Kidamycinone by Means of Two Regioselective Diels–Alder Reactions

An efficient access for the synthesis of pluramycinones is described. Total syntheses of racemic γ-indomycinone and kidamycinone were achieved by means of two Diels–Alder reactions. A first Diels–Alder condensation followed by a Stille cross-coupling is used for the elaboration of the desired substi...

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Veröffentlicht in:Journal of organic chemistry 2017-06, Vol.82 (11), p.5710-5719
Hauptverfasser: Mabit, Thibaud, Siard, Aymeric, Pantin, Mathilde, Zon, Doumadé, Foulgoc, Laura, Sissouma, Drissa, Guingant, André, Mathé-Allainmat, Monique, Lebreton, Jacques, Carreaux, François, Dujardin, Gilles, Collet, Sylvain
Format: Artikel
Sprache:eng
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Chemical Sciences
Medicinal Chemistry
Organic chemistry
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Zusammenfassung:An efficient access for the synthesis of pluramycinones is described. Total syntheses of racemic γ-indomycinone and kidamycinone were achieved by means of two Diels–Alder reactions. A first Diels–Alder condensation followed by a Stille cross-coupling is used for the elaboration of the desired substituted dienes which will be involved in the second pericyclic reaction with juglone to construct the tetracyclic core of pluramycinones.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00544