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| Author(s): |
Rodrigo Cella
Total Authors: 1
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| Document type: | Doctoral Thesis |
| Press: | São Paulo. |
| Institution: | Universidade de São Paulo (USP). Conjunto das Químicas (IQ e FCF) (CQ/DBDCQ) |
| Defense date: | 2008-01-15 |
| Examining board members: |
Hélio Alexandre Stefani;
Antônio Luiz Braga;
Liliana Marzorati;
Nicola Petragnani;
Paulo Henrique Schneider
|
| Advisor: | Hélio Alexandre Stefani |
| Abstract | |
This thesis describes, in two different chapters, the asymmetric synthesis of malevamide D and the application of organotellurium compounds in Suzuki-Miyaura reaction. The first chapter refers to the asymmetric synthesis of malevamide D, a natural depsipeptide which belongs to the dolastatins family, and these compounds have a great interest due to theirs citotoxic activities. The DAP and MMMAH units were reached in excellent yields and stereoselectivities from 1,2-addition reaction of potassium crotyl or allyltrifluoroborate to aldehydes derivate from L-proline and L-isoleucine, respectively. The malevamide D elongation was made from reaction of esterification and amidation, unfortunately it was not possible finish the synthesis due to some problems in the last step of the total synthesis. The second chapter describes the reaction between aryl or vinyl tellurides and potassium organotrifluoroborate salts, mediated by a palladium catalyst. From this cross-coupling reaction type Suzuki-Miyaura was possible obtain 1,3-dienes, biarylic systems, (E)- or (Z)-stylbenes and 1,3-dienes. Al reactions showed to be tolerant to a wide range of functional groups and highly stereoconservative, in the cases involving vinylic substrates. (AU) | |