Organocatalytic Approaches to the Enantioselective Synthesis of Stemona Alkaloids

• Grant number: 18/05742-9
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• Start date: June 01, 2018
• End date: July 31, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Ronaldo Aloise Pilli
• Grantee: Bruno Matos Paz
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

We aim to investigate organocatalyzed approaches to the asymmetric synthesis of alkaloids isolated from herbal extracts of plants of the Stemonaceae family which have been employed in the asian folk medicine. We plan to develop methodologies for the enantioselective synthesis of alkaloids from the stemoamide, tuberostemospironine and parvistemoline groups based on the chemistry of cyclic N-acyliminium ions with limited use of protecting groups. For the synthesis of stemoamide and sessilifoliamides B-D, the strategy to be employed is based on chiral enamine catalysis and for the alkaloids of the tuberostemospironine group, silyloxyfurans will be used as nucleophiles and chiral thioureas and phosphoric acids will be investigated as catalysts.

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)

BERNARDI ROSSO, GIOVANNI; MATOS PAZ, BRUNO; ALOISE PILLI, RONALDO. Formal Syntheses of (+/-)-Tuberostemospiroline and (+/-)-Stemona-lactam R and Total Synthesis of (+/-)-Stemoamide. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2022, n. 28, p. 6-pg., 2022-07-27. (19/13104-5, 18/05742-9)