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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Synthetic Studies toward the Total Synthesis of Tautomycetin

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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