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2-(Trialkylsilyl)aryl trifluoromethanesulfonates as aryne precursors in the development of methodologies for obtaining nitrogen-containing heterocyclic compounds and total syntheses of bioactive natural products

Grant number: 17/21990-0
Support type:Regular Research Grants
Duration: February 01, 2018 - January 31, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Cristiano Raminelli
Grantee:Cristiano Raminelli
Home Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil

Abstract

The benzyne chemistry has found applications in organic chemistry, including total syntheses of natural products and preparations of functional materials. In this sense, 2-(trimethylsilyl)aryl trifluoromethanesulfonates emerge as an important alternative for the formation of benzyne and derivatives, under mild reaction conditions, enlarging the scope of benzyne chemistry applications in preparative organic chemistry. In this context, we aim to develop a synthetic route that employs organometallic catalysis, avoiding the use of n-butyllithium, a strongly basic and nucleophilic reagent, in the preparation of functionalized 2-(triethylsilyl)aryl triflates. In addition, we intend to use 2-(trimethylsilyl)aryl triflates in the development of methodologies to obtain nitrogen-containing heterocyclic compounds, namely, isoquinolines and dehydroaporphines, and in total syntheses of bioactive natural products, including three non-chiral anthraquinones, represented by morindaparvin A, as well as two protoberberine alkaloids, (S)-tetrahydropalmatine and (+)-coridaline, and one aporphine alkaloid, (S)-nuciferine, exploring enantioselective hydrogenations as approach for the introduction of chirality. (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)
CORREA, BIANCA K.; SILVA, TAMIRIS R. C.; RAMINELLI, CRISTIANO. Total syntheses of (+)-bernumidine and its unnatural enantiomer. Clinica Chimica Acta, v. 485, p. 3583-3585, OCT 2018. Web of Science Citations: 0.
CORREA, BIANCA K.; SILVA, TAMIRIS R. C.; RAMINELLI, CRISTIANO. Total syntheses of (+)-bernumidine and its unnatural enantiomer. Tetrahedron Letters, v. 59, n. 39, p. 3583-3585, SEP 26 2018. Web of Science Citations: 0.

Please report errors in scientific publications list by writing to: cdi@fapesp.br.