Asymmetric synthesis of new gamma-butenolides via organocatalyzed epoxidation of chalcones

Author(s)

Vieira, Lucas C. C. ; Matsuo, Bianca T. ; Martelli, Lorena S. R. ; Gall, Mayara ; Paixao, Marcio W. ; Correa, Arlene G.

• Document type: Journal article
• Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 15, n. 29, p. 6098-6103, AUG 7 2017.
• Web of Science Citations: 3

Abstract

gamma-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted gamma-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched gamma-butenolides in moderate overall yield and good enantiomeric excess. (AU)

• FAPESP's process: 15/17141-1 - Development and Mechanism Studies of New Synthetic Methodologies for the Synthesis of Bioactive Compounds.
• Grantee: Ricardo Samuel Schwab
• Support Opportunities: Regular Research Grants
• 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: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC