A biomimetic approach to the total synthesis of Stemona alkaloids

• Grant number: 16/12541-4
• Support Opportunities: Regular Research Grants
• Start date: September 01, 2016
• End date: August 31, 2018
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Ronaldo Aloise Pilli
• Grantee: Ronaldo Aloise Pilli
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

The total synthesis of representatives of the Stemona alkaloids is proposed based on a biossynthetic rationale. Our synthetic efforts will be directed to the synthesis of racemic tuberostemospironine, stemolactam R, tuberostemospiroline, croomine and sessilifoliamide J. Our approach is based on the intramolecular tandem vinylogous Mannich cyclization reaction of a silyloxyfuran and an iminium ion, generated in situ via reduction of the corresponding azide. An asymmetric version of the intramolecular tandem vinylogous Mannich cyclization reaction based on chiral Bronsted acids will be also explored. In addition to explore a novel approach to the synthesis of Stemona alkaloids, this proposal aims to support the cytotoxic evaluation of this family of natural products which so far has not received much attention from the scientific community. (AU)

Scientific publications

(9)

(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)

DELLA-FELICE, FRANCO; SAROTTI, ARIEL M.; KRISCHE, MICHAEL J.; PILLI, RONALDO A.. Total Synthesis and Structural Validation of Phosdiecin A via Asymmetric Alcohol-Mediated Carbonyl Reductive Coupling. Journal of the American Chemical Society, v. 141, n. 35, p. 13778-13782, SEP 4 2019. (17/18487-4, 16/12541-4, 13/07607-8, 14/25474-8)

DELLA-FELICE, FRANCO; DE ASSIS, FRANCISCO F.; SAROTTI, ARIEL M.; PILLI, RONALDO A.. Palladium-Catalyzed Formation of Substituted Tetrahydropyrans: Mechanistic Insights and Structural Revision of Natural Products. SYNTHESIS-STUTTGART, v. 51, n. 7, p. 1545-1560, APR 2019. (13/07607-8, 16/12541-4, 14/25474-8)

SILVA, MARCELA C. R.; VILELA, ADRIANA F. L.; CARDOSO, CARMEN L. L.; PILLI, RONALDO A. A.. Synthesis and Anticholinesterase Evaluation of Cassine, Spectaline and Analogues. SCIENTIA PHARMACEUTICA, v. 90, n. 4, p. 21-pg., 2022-01-01. (14/50249-8, 19/13104-5, 16/02873-0, 16/12541-4)

PILLI, RONALDO ALOISE; DE TOLEDO, IAN; MEIRELLES, MATHEUS ANDRADE; GRIGOLO, THIAGO AUGUSTO. Goniothalamin-Related Styryl Lactones: Isolation, Synthesis, Biological Activity and Mode of Action. Current Medicinal Chemistry, v. 26, n. 41, p. 7372-7451, 2019. (16/12541-4, 13/07607-8)

DELLA-FELICE, FRANCO; BARTOLOMEU, ALOISIO DE ANDRADE; PILLI, RONALDO ALOISE. The phosphate ester group in secondary metabolites. NATURAL PRODUCT REPORTS, v. 39, n. 5, p. 42-pg., 2022-04-14. (16/12541-4, 14/25474-8, 19/13104-5, 13/07607-8, 20/07991-6)

DELLA-FELICE, FRANCO; PILLI, RONALDO A.; SAROTTI, ARIEL M.. Computer-Guided Total Synthesis of Natural Products. Recent Examples and Future Perspectives. Journal of the Brazilian Chemical Society, v. 29, n. 5, p. 1041-1075, MAY 2018. (14/25474-8, 16/12541-4, 13/07607-8)

RAITZ, ISMAEL; DE SOUZA FILHO, ROBERTO Y.; DE ANDRADE, LORENA P.; CORREA, JOSE R.; NETO, BRENNO A. D.; PILLI, RONALDO A.. Preferential Mitochondrial Localization of a Goniothalamin Fluorescent Derivative. ACS OMEGA, v. 2, n. 7, p. 3774-3784, JUL 2017. (09/51602-5, 16/12541-4, 13/07607-8)

-FELICE, FRANCO DELLA; SAROTTI, ARIEL M.; PILLI, RONALDO A.. Catalytic Asymmetric Synthesis and Stereochemical Revision of (+)-Cryptoconcatone H. Journal of Organic Chemistry, v. 82, n. 17, p. 9191-9197, SEP 1 2017. (14/25474-8, 16/12541-4, 13/07607-8)

PILLI, RONALDO A.; DE ASSIS, FRANCISCO F.. Organic Synthesis: New Vistas in the Brazilian Landscape. Anais da Academia Brasileira de Ciências, v. 90, n. 1, 1, p. 895-941, 2018. (13/07607-8, 16/12541-4, 16/08569-0, 17/06836-4)