Study of the Stereoselectivity in Ring Closing Metathesis Applied to Decalactones

• Grant number: 11/14760-1
• Support Opportunities: Scholarships in Brazil - Master
• Start date: April 01, 2012
• End date: March 31, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Luiz Sidney Longo Junior
• Grantee: Willian Tawata
• Host Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil
• Associated research grant: 07/07338-6 - Studies towards the synthesis of decalactones, AP.JP

Abstract

This project describes the study of the E/Z stereoselectivity os reactions of ring closing metathesis apllied to the construction of decalactones which are important moiety present in several natural products bearing interesting biological activities. The RCM reactions will be conducted in different reactional conditions (classical and nonclassical), using the most common commercially available catalysts (1st and 2nd Grubbs and Hoveyda-Grubbs), comparing the results obtained with de relative stability of a series of decalactones (different C=C positions in the ring). The stabilities will be obtained via Theoretical Calculations using HF and B3LYP bases. The influence of protective groups of allylic hydroxyl group on the outcome of the reaction will also be studied.