Synthetic studies toward the total synthesis of tautomycetin
Danilo Pereira de Sant'Ana, Celso de Oliveira Rezende Junior, Jean-Marc Campagne, Luiz Carlos Dias, Renata Marcia de Figueiredo
ARTIGO
Inglês
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...
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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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DOI: https://doi.org/10.1021/acs.joc.9b01712
Texto completo: https://pubs.acs.org/doi/10.1021/acs.joc.9b01712
Synthetic studies toward the total synthesis of tautomycetin
Danilo Pereira de Sant'Ana, Celso de Oliveira Rezende Junior, Jean-Marc Campagne, Luiz Carlos Dias, Renata Marcia de Figueiredo
Synthetic studies toward the total synthesis of tautomycetin
Danilo Pereira de Sant'Ana, Celso de Oliveira Rezende Junior, Jean-Marc Campagne, Luiz Carlos Dias, Renata Marcia de Figueiredo
Fontes
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The journal of organic chemistry Vol. 84, no. 19 (Oct., 2019), p. 12344, n. art. 12357 |