Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

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
Doumadé Zon, Laura Foulgoc, Jacques Lebreton, François Carreaux, Gilles Dujardin, Thibaud Mabit, Mathilde Pantin, Monique Mathé-Allainmat, André Guingant, Sylvain Collet, Aymeric Siard, Drissa Sissouma
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00544

DOI: 10.1021/acs.joc.7b00544

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