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| Author(s): |
Luiz Fernando Toneto Novaes
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: | 2019-07-05 |
| Examining board members: |
Júlio Cezar Pastre;
Carlos Roque Duarte Correia;
Emilio Carlos de Lucca Júnior;
Antonio Carlos Bender Burtoloso;
Timothy John Brocksom
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| Advisor: | Júlio Cezar Pastre |
| Abstract | |
In chapter 1, a brief introduction about terpenes and meroterpenes is presented, showing biosynthetic considerations, and differences between classical synthesis of selected natural products and synthetic approachs reported during the last decade. In chapter 2, we describe our efforts toward the synthesis of the marine meroterpene actinoranone, natural product isolated from a new species of Streptomyces which displayed in vitro cytotoxicity against human colon câncer (HCT-116). The terpenoid fragment was concluded in nine steps, with sclareolide as starting material. The polyketide fragment was synthesized in nine steps, with 3,5-dimethoxybenzaldehyde as starting material. The fragments coupling and conclusion of the formal synthesis was reported. This synthesis used concepts such as redox economy and minimization of protecting groups, in order to achieve a more concise synthesis. In chapter 3, the synthesis of norsesquiterpene guaiane pleocarpanone was studied. Our approach demanded 8 steps, and could be performed without protecting groups and few redox steps. However, this approach still is not ideal, since the 1,4 conjugate addition step furnishes low selectivity, which makes it difficult to characterize and obtain the products in pure form. This work open doors to a more concise synthesis of pleocarpanone, however, additional optimizations are necessary. In chapter 4, we report our efforts to expand the use of an oxidative strategy to synthesize highly oxidized sesquiterpenes isolated from Illicium genus from cedrol, a sesquiterpene with a low oxidation degree. The syntheses of natural products 3-deoxy-pseudoanisatin and 3,4-dehydrofloridanolide were concluded in eleven and fifteen steps, respectively. New reactivities found during the development of this work were discussed (AU) | |
| FAPESP's process: | 15/08199-6 - Application of Dioxiranes in continuous flow, synthesis of Actinoranone and decalin fragment of Azadirachtin |
| Grantee: | Luiz Fernando Toneto Novaes |
| Support Opportunities: | Scholarships in Brazil - Doctorate |