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

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posted on 11.05.2017, 00:00 by Thibaud Mabit, Aymeric Siard, Mathilde Pantin, Doumadé Zon, Laura Foulgoc, Drissa Sissouma, André Guingant, Monique Mathé-Allainmat, Jacques Lebreton, François Carreaux, Gilles Dujardin, Sylvain Collet
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.

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