| Texto completo | |
| Autor(es): |
de Sant'Ana, Danilo Pereira
[1, 2, 3]
;
Rezende Junior, Celso de Oliveira
[1, 4]
;
Campagne, Jean-Marc
[2]
;
Dias, Luiz Carlos
[1]
;
de Figueiredo, Renata Marcia
[2]
Número total de Autores: 5
|
| Afiliação do(s) autor(es): | [1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil
[2] Univ Montpellier, UMR 5253, Inst Charles Gerhardt, CNRS, ENSCM, 240 Ave Prof Emile Jeanbrau, F-34296 Montpellier 5 - France
[3] Eurofarma 3-565, Presidente Castelo Branco Highway, BR-06696000 Itapevi, SP - Brazil
[4] Univ Fed Uberlandia, Inst Chem, BR-38400902 Uberlandia, MG - Brazil
Número total de Afiliações: 4
|
| Tipo de documento: | Artigo Científico |
| Fonte: | Journal of Organic Chemistry; v. 84, n. 19, p. 12344-12357, OCT 4 2019. |
| Citações Web of Science: | 0 |
| Resumo | |
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. (AU) | |
| Processo FAPESP: | 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock |
| Beneficiário: | Arlene Gonçalves Corrêa |
| Modalidade de apoio: | Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia |
| Processo FAPESP: | 15/08541-6 - Ressonância magnética nuclear: além da determinação estrutural |
| Beneficiário: | Claudio Francisco Tormena |
| Modalidade de apoio: | Auxílio à Pesquisa - Temático |
| Processo FAPESP: | 12/11220-9 - Síntese do fragmento anidrido da tautomicetina |
| Beneficiário: | Danilo Pereira de Sant'Ana |
| Modalidade de apoio: | Bolsas no Exterior - Estágio de Pesquisa - Doutorado |