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
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Schlagworte:	Chemical Sciences Medicinal Chemistry Organic chemistry
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container_title	Journal of organic chemistry
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creator	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
description	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.
doi_str_mv	10.1021/acs.joc.7b00544
format	Article
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subjects	Chemical Sciences Medicinal Chemistry Organic chemistry
title	Total Synthesis of γ‑Indomycinone and Kidamycinone by Means of Two Regioselective Diels–Alder Reactions
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