Iodine and hypervalent iodine in the synthesis of molecules with biological activity

• Grant number: 10/16042-6
• Support Opportunities: Regular Research Grants
• Start date: November 01, 2010
• End date: October 31, 2013
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Luiz Fernando da Silva Júnior
• Grantee: Luiz Fernando da Silva Júnior
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
• City of the host institution: São Paulo
• Associated researchers: Kishore Kumar Reddy Kachi Reddy ; Rafael Ribeiro da Silva Soares

Abstract

This research proposal aims to investigate applications of iodine and of hypervalent iodine in the synthesis of molecules with biological activity. In this context, we will continue to investigate the oxidation of 1,2-dihydronaphthalenes by iodine(III) reagents to obtain functionalized indanes. An asymmetric version of this reaction will also be investigated using chiral iodine(III) reagents. Moreover, using as key step a ring contraction reaction promoted by iodine(III), the total synthesis of (+)-trans-trikentrin A, of (+)-indatraline, and of (±)-irindalone will be achieved. The iodine-catalyzed Prins and aza-Prins cyclization will be investigated. This reaction will be applied in the asymmetric total synthesis of the natural product populene D, whose synthesis has not been reported. (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

LEMOS SILVA, SIGUARA BASTOS; DELLA TORRE, ADRIANA; DE CARVALHO, JOAO ERNESTO; TASCA GOIS RUIZ, ANA LUCIA; SILVA, JR., LUIZ F.. Seven-Membered Rings through Metal-Free Rearrangement Mediated by Hypervalent Iodine. Molecules, v. 20, n. 1, p. 1475-1494, JAN 2015. (12/10568-1, 10/16042-6)