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Synthesis of unsaturated bicyclic lactones via sulfur ylides

Grant number: 18/17244-3
Support type:Scholarships in Brazil - Scientific Initiation
Effective date (Start): November 01, 2018
Effective date (End): October 31, 2019
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Antonio Carlos Bender Burtoloso
Grantee:Tharik Azis Castrequini Dahwache
Home Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

Abstract

This project aims to evaluate methodologies for the synthesis of unsaturated bicyclic lactones through the Corey-Chaykovsky reaction, followed by elimination-epoxide opening. The methodology to be evaluated has already been applied in our laboratory for the synthesis of the unsaturated bicyclic lactone 5,5-dimethyltetrahydroisocromen-3(4H)-one, in 35% yield. The project aims to optimize the reaction conditions and increase the substrate scopes, covering different substituents and sizes of the rings.