About the synthesis of furanoheliangolides through the Diels-Alder reaction
Full text
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| Author(s): |
Valquiria Aragão
Total Authors: 1
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| Document type: | Master's Dissertation |
| Press: | Ribeirão Preto. |
| Institution: | Universidade de São Paulo (USP). Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto (PCARP/BC) |
| Defense date: | 2003-04-11 |
| Examining board members: |
Mauricio Gomes Constantino;
Alberto Federman Neto;
Liliana Marzorati
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| Advisor: | Mauricio Gomes Constantino |
| Abstract | |
Furanoheliangolides are biologically active natural products containing a 11-oxabicyclo[6.2.1]undecane skeleton. In this work we have investigated two different approaches to synthesize a model of the core structure of goyazensolide. Both approaches involve a Diels-Alder reaction and a bond breaking reaction to produce the polycyclic structure. In the first proposal we prepared mesylate compound. Attempts to effect an elimination reaction, however, resulted either in complex mixture or in undesired products. In the second proposal we prepared ester and investigated two alternative paths, out of several possibilities, to proceed the synthesis. In the first, ester was hydrolyzed to acid, but it was not possible to obtain the corresponding Weinreb amide. In the second path the ester was reduced to alcohol, that was oxidized to aldehyde; this, when treated with the anion from hydrazone, furnished hydrazone instead of the expected product of carbanion addition. Further studies should be developed in the future. (AU) | |