Total Synthesis and Tentative Structural Elucidation of Cryptomoscatone E3: Interplay of Experimental and Computational Studies

Author(s)

Novaes, Luiz F. T. ^[1] ; Sarotti, Ariel M. ^[2] ; Pilli, Ronaldo A. ^[1]

Affiliation

^[1] Univ Estadual Campinas Unicamp, Inst Quim, Dept Quim Organ, BR-13084971 Campinas, SP - Brazil

^[2] Univ Nacl Rosario, CONICET, Fac Ciencias Bioquim & Farmaceut, Inst Quim Rosario, RA-2000 Rosario, Santa Fe - Argentina

• Document type: Journal article
• Source: Journal of Organic Chemistry; v. 80, n. 24, p. 12027-12037, DEC 18 2015.
• Web of Science Citations: 22

Abstract

A successful combination of computational chemistry and total synthesis was explored to tentatively elucidate the absolute configuration of cryptomoscatone E3, a polyketide isolated from the Brazilian tree Cryptocarya mandiocanna. Two independent synthetic approaches are discussed based on asymmetric allylation, ring closing metathesis, and aldol reactions. (AU)

• FAPESP's process: 09/51602-5 - Chemical biology: new natural and synthetic molecular targets against cancer, structural studies, biological evaluation and mode of action
• Grantee: Ronaldo Aloise Pilli
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 13/07607-8 - OCRC - Obesity and Comorbidities Research Center
• Grantee: Licio Augusto Velloso
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC