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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.)

Palladium-Catalyzed Formation of Substituted Tetrahydropyrans: Mechanistic Insights and Structural Revision of Natural Products

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Della-Felice, Franco [1] ; de Assis, Francisco F. [1] ; Sarotti, Ariel M. [2] ; Pilli, Ronaldo A. [1]
Total Authors: 4
[1] Univ Estadual Campinas, Inst Chem, BR-13084971 Campinas, SP - Brazil
[2] Univ Nacl Rosario CONICET, Fac Ciencias Bioquim & Farmaceut, Inst Quim Rosario, Suipacha 531, S2002 LRK, Rosario, Santa Fe - Argentina
Total Affiliations: 2
Document type: Journal article
Source: SYNTHESIS-STUTTGART; v. 51, n. 7, p. 1545-1560, APR 2019.
Web of Science Citations: 0

A comprehensive study on the stereochemical outcome of palladium-catalyzed formation of 2,4,6-trisubstituted tetrahydropyrans through cyclization of the corresponding allylic acetates using both Pd(0) and Pd(II) catalysts is presented. We have found that the stereochemical outcome of this cyclization is dependent not only on the stereochemistry of the acyclic precursor but also on the nature of the palladium catalyst. These results were applied to the total synthesis of the putative structure of cryptoconcatone H. Experimental and computational DP4+ NMR results were used to assess the structures proposed for cryptoconcatones K and L. (AU)

FAPESP's process: 13/07607-8 - OCRC - Obesity and Comorbidities Research Center
Grantee:Licio Augusto Velloso
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 16/12541-4 - A biomimetic approach to the total synthesis of Stemona alkaloids
Grantee:Ronaldo Aloise Pilli
Support type: Regular Research Grants
FAPESP's process: 14/25474-8 - Synthesis and biological evualuation of Brevipolide A, Cryptomoskatone F1 and related compounds
Grantee:Franco Della Felice
Support type: Scholarships in Brazil - Doctorate (Direct)