An article Synthetic Studies toward the Total Synthesis of Tautomycetin WOS:000489201000010 published article about STEREOSELECTIVE ALDOL CONDENSATIONS; MALEIC-ANHYDRIDE SEGMENT; ABSOLUTE-CONFIGURATION; ADDITION-REACTIONS; REAGENTS; IMMUNOSUPPRESSANT; CHEMISTRY; KETONES; ESTERIFICATION; BIOSYNTHESIS in [de Sant’Ana, Danilo Pereira; Rezende Junior, Celso de Oliveira; Dias, Luiz Carlos] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazil; [de Sant’Ana, Danilo Pereira; Campagne, Jean-Marc; de Figueiredo, Renata Marcia] Univ Montpellier, UMR 5253, Inst Charles Gerhardt, CNRS,ENSCM, 240 Ave Prof Emile Jeanbrau, F-34296 Montpellier 5, France; [de Sant’Ana, Danilo Pereira] Eurofarma 3-565,Presidente Castelo Branco Highway, BR-06696000 Itapevi, SP, Brazil; [Rezende Junior, Celso de Oliveira] Univ Fed Uberlandia, Inst Chem, BR-38400902 Uberlandia, MG, Brazil in 2019, Cited 60. The Name is Benzoic anhydride. Through research, I have a further understanding and discovery of 93-97-0. Product Details of 93-97-0
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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