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 - Organic Chemistry
• Principal researcher: 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.