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Organocatalytic Approaches to the Enantioselective Synthesis of Stemona Alkaloids

Grant number: 18/05742-9
Support type:Scholarships in Brazil - Post-Doctorate
Effective date (Start): June 01, 2018
Effective date (End): July 31, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal researcher:Ronaldo Aloise Pilli
Grantee:Bruno Matos Paz
Home 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.

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