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Title: Common scaffolds for the enantioselective synthesis of marine, plant, and amphibian cis-decahydroquinoline alkaloids
Author: Pinto, Alexandre
Director/Tutor: Amat Tusón, Mercedes
Griera Farres, Rosa
Keywords: Productes naturals
Catàlisi asimètrica
Síntesi de fàrmacs
Natural products
Enantioselective catalysis
Drug synthesis
Issue Date: 28-Sep-2017
Publisher: Universitat de Barcelona
Abstract: [eng] Chiral amino alcohol derived lactams are a valuable scaffold for the enantioselective synthesis of alkaloids. In the present thesis the potential of this methodology was expanded and to demonstrate the synthetic utility of chiral tricyclic lactams obtainedthe enantioselective total synthesis complex cis-decahydroquinoline alkaloids was carried out. The alkaloids that were targeted for synthesis using the developed methodology were the lepadin alkaloids (marine alkaloids) and tricyclic cis-decahydroquinoline alkaloids such as cermizine B (Lycopodium alkaloids). To accomplish these objectives further studies on the functionalization of the decahydroquinoline system were required in order to install the appropriate substituents and functionalities for the synthesis of each target. During the present PhD thesis it was possible to complete the total synthesis of (+)-gephyrotoxin 287C, (−)-cermizine B, (−)-lepadin B and (+)-lepadin D and the formal total synthesis of (−)-lepadins A and C.
Appears in Collections:Tesis Doctorals - Departament - Farmacologia, Toxicologia i Química Terapèutica

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