| Full text | |
| Author(s): |
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]
Total Authors: 5
|
| Affiliation: | [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
Total Affiliations: 4
|
| Document type: | Journal article |
| Source: | Journal of Organic Chemistry; v. 84, n. 19, p. 12344-12357, OCT 4 2019. |
| Web of Science Citations: | 0 |
| 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. (AU) | |
| FAPESP's process: | 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock |
| Grantee: | Arlene Gonçalves Corrêa |
| Support Opportunities: | Research Grants - Research Centers in Engineering Program |
| FAPESP's process: | 15/08541-6 - Nuclear magnetic resonance spectroscopy: beyond molecular structure assignment |
| Grantee: | Claudio Francisco Tormena |
| Support Opportunities: | Research Projects - Thematic Grants |
| FAPESP's process: | 12/11220-9 - Synthesis of anhydride fragment from tautomycetin |
| Grantee: | Danilo Pereira de Sant'Ana |
| Support Opportunities: | Scholarships abroad - Research Internship - Doctorate |