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| Author(s): |
Franco Della Felice
Total Authors: 1
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| Document type: | Doctoral Thesis |
| Press: | Campinas, SP. |
| Institution: | Universidade Estadual de Campinas (UNICAMP). Instituto de Química |
| Defense date: | 2019-10-16 |
| Examining board members: |
Ronaldo Aloise Pilli;
Paulo Roberto Ribeiro Costa;
Antonio Carlos Bender Burtoloso;
Carlos Roque Duarte Correia;
Igor Dias Jurberg
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| Advisor: | Ronaldo Aloise Pilli |
| Abstract | |
Herein we described our synthetic efforts towards the total synthesis and structural validation of type I polyketides brevipolide A, cryptoconcatones H, K and L and phosdiecin A isolated from "Hyptis brevipes", "Cryptocarya concinna" e Streptomyces sp". SS99BA-2, respectively. Our synthetic efforts towards brevipolide A and the first enantioselective total synthesis and structural confirmation of cryptoconcatone H (12 steps, 3.6% yield) and phosdiecin A (13 steps, 0.87-1.0% yield) are presented. A structural revision of cryptoconcatone K and L is also discussed. Since the final configuration of these natural products were uncertain, the assessment of the most likely structures were guided by computational studies based on NMR parameters. In order to develop convergent, step-efficient synthetic routes, the synthesis of these natural products envisaged the application of modern catalytic asymmetric methodologies: Sharpless asymmetric epoxidation, ruthenium-mediated olefin metathesis, Suzuki-Miyaura coupling, palladium-mediated allylic substitution and iridium-mediated carbonyl allylations, among others (AU) | |
| FAPESP's process: | 14/25474-8 - Synthesis and biological evualuation of Brevipolide A, Cryptomoskatone F1 and related compounds |
| Grantee: | Franco Della Felice |
| Support Opportunities: | Scholarships in Brazil - Doctorate (Direct) |