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Synthetic Studies toward the Total Synthesis of Tautomycetin

Abstract : The studies culminating in the synthesis of two large subunits of tautomycetin are described. The first one, fragment C1–C12 that has an anti-1,3-dimethyl system and a terminal diene unit, was accomplished in 10 linear steps in 7.4% overall yield. The second one, fragment C13–C25 which bears the sensitive anhydride framework and the majority of the stereogenic centers, was prepared in 13 linear steps (longest sequence) in 8% overall yield. Among the key transformations used, a regioselective epoxide opening, a Pd-catalyzed addition of terminal alkyne to acceptor alkyne, a Mukaiyama aldol reaction, a Yamaguchi esterification, and a homemade mild di-esterification can be cited. The chosen strategies allowed good yields, stereoselectivity, reproducibility, and scalability for several important intermediates.
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https://hal.umontpellier.fr/hal-02334465
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Soumis le : samedi 26 octobre 2019 - 16:24:17
Dernière modification le : dimanche 27 octobre 2019 - 01:17:12

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Danilo Pereira de Sant’ana, Celso de Oliveira Rezende Júnior, Jean-Marc Campagne, Luiz Carlos Dias, Renata Marcia de Figueiredo. Synthetic Studies toward the Total Synthesis of Tautomycetin. Journal of Organic Chemistry, American Chemical Society, 2019, 84 (19), pp.12344-12357. ⟨10.1021/acs.joc.9b01712⟩. ⟨hal-02334465⟩

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