Tesi etd-07222020-105432 |
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Tipo di tesi
Tesi di laurea magistrale
Autore
PINCIAROLI, SIMONE
URN
etd-07222020-105432
Titolo
A New Approach to the Enantioselective Synthesis of the Bioactive Natural Product Zoapatanol
Dipartimento
CHIMICA E CHIMICA INDUSTRIALE
Corso di studi
CHIMICA
Relatori
relatore Prof.ssa Di Bussolo, Valeria
relatore Prof. Clark, Stephen
relatore Prof. Clark, Stephen
Parole chiave
- Asymmetric Tsuji-Trost Allylation
- Enantioselective Synthesis
- RCM
- Total Synthesis
Data inizio appello
14/09/2020
Consultabilità
Non consultabile
Data di rilascio
14/09/2090
Riassunto
(+)-Zoapatanol is a bioactive natural product found during the 80’s in Montanoa tomentosa leaves, a mexican plant. Showing a synthetically challenging structure and an important biological activity, an enantioselective synthesis was outlined, based on the few papers published since the compound was discovered. The previously reported synthetic pathways are plagued by an elevated number of steps and/or poor yields, making a general rethinking towards the Total Synthesis of this natural product necessary.
Considering also previous attempts and studies towards the synthesis of (+)-Zoapatanol made by Prof. S. J. Clark’s research group, in this work a new asymmetric pathway was envisaged, trying to face and solve the main problems that were plaguing other synthetic approaches. A solid route towards one of the key intermediates was successfully achieved, opening a new pathway, hypothetically shorter and generally improved, respect the ones already present in the literature.
Considering also previous attempts and studies towards the synthesis of (+)-Zoapatanol made by Prof. S. J. Clark’s research group, in this work a new asymmetric pathway was envisaged, trying to face and solve the main problems that were plaguing other synthetic approaches. A solid route towards one of the key intermediates was successfully achieved, opening a new pathway, hypothetically shorter and generally improved, respect the ones already present in the literature.
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