Application of Dioxiranes in continuous flow, synthesis of Actinoranone and decalin fragment of Azadirachtin

• Grant number: 15/08199-6
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: August 01, 2015
• End date: July 31, 2019
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Agreement: Coordination of Improvement of Higher Education Personnel (CAPES)
• Principal Investigator: Júlio Cezar Pastre
• Grantee: Luiz Fernando Toneto Novaes
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated scholarship(s): 17/18029-6 - Synthesis of Complex Antibiotics Inspired by Natural Products, BE.EP.DR

Abstract

The project proposes a simplification of synthesis of dioxiranes, and the use in C-H oxidations under continuous flow conditions. We also propose the total synthesis and structural elucidation of meroterpenoid actinoranone. Furthermore, we intend to explore the synthesis of the decalin fragment of azadirachtin by a bioinspired approach: from the terpene sclareolide would be performed eight selective oxidations to achieve the fragment in a route potentially more efficient that the one used by Ley and coworkers in the total synthesis of this natural product. (AU)

Scientific publications

(7)

(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)

ALONSO, ISABELLA G.; YAMANE, LAIS T.; DE FREITAS-BLANCO, VERONICA S.; NOVAES, LUIZ F. T.; FRANZ-MONTAN, MICHELLE; DE PAULA, ENEIDA; RODRIGUES, MARILI V. N.; RODRIGUES, RODNEY A. F.; PASTRE, JULIO C.. A new approach for the total synthesis of spilanthol and analogue with improved anesthetic activity. Tetrahedron, v. 74, n. 38, p. 5192-5199, SEP 20 2018. (15/08199-6, 14/06461-2, 14/25770-6, 14/16186-9, 14/26378-2)

NOVAES, LUIZ F. T.; GONCALVES, KALIANDRA DE ALMEIDA; TRIVELLA, DANIELA B. B.; PASTRE, JULIO C.. Formal Total Synthesis of Actinoranone: Synthesis Approaches and Cytotoxic Studies. Journal of Organic Chemistry, v. 83, n. 9, p. 5160-5176, MAY 4 2018. (15/08199-6, 14/25770-6, 14/26378-2)

LUIZ F. T. NOVAES; JULIO C. PASTRE. AVANÇOS RECENTES NA HIDROAMINAÇÃO DE COMPOSTOS INSATURADOS. Química Nova, v. 40, n. 8, p. 932-945, 2017-09-00. (14/25770-6, 15/08199-6, 14/26378-2)

FORNI, JOSE AUGUSTO; TONETO NOVAES, LUIZ FERNANDO; GALAVERNA, RENAN; PASTRE, JULIO C.. Novel polystyrene-immobilized chiral amino alcohols as heterogeneous ligands for the enantioselective arylation of aldehydes in batch and continuous flow regime. CATALYSIS TODAY, v. 308, n. SI, p. 86-93, JUN 15 2018. (14/26093-8, 15/08199-6, 14/25770-6, 14/26378-2)

SANTOS, CARLA C. F.; PARADELA, LUCIANA S.; NOVAES, LUIZ F. T.; DIAS, SANDRA M. G.; PASTRE, JULIO C.. Design and synthesis of cenocladamide analogues and their evaluation against breast cancer cell lines. MedChemComm, v. 8, n. 4, p. 755-766, APR 1 2017. (15/08199-6, 14/25770-6, 14/26378-2, 14/15968-3)

NOVAES, LUIZ F. T.; PASTRE, JULIO C.. Formal Total Synthesis of Actinoranone and Asymmetric Synthesis of Labda-7,13-(E)-dien-15-ol. ORGANIC LETTERS, v. 19, n. 12, p. 3163-3166, JUN 16 2017. (15/08199-6, 14/25770-6, 14/26378-2)

FORNI, JOSE AUGUSTO; TONETO NOVAES, LUIZ FERNANDO; GALAVERNA, RENAN; PASTRE, JULIO C.. Novel polystyrene-immobilized chiral amino alcohols as heterogeneous ligands for the enantioselective arylation of aldehydes in batch and continuous flow regime. CATALYSIS TODAY, v. 308, p. 8-pg., 2018-06-15. (15/08199-6, 14/26378-2, 14/25770-6, 14/26093-8)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

NOVAES, Luiz Fernando Toneto. Total synthesis of terpenes and meroterpenes: actinoranone, pleocarpanone and Illicium sesquiterpenes. 2019. Doctoral Thesis - Universidade Estadual de Campinas (UNICAMP). Instituto de Química Campinas, SP.