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| Author(s): |
Airton Gonçalves Salles Junior
Total Authors: 1
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| Document type: | Master's Dissertation |
| Press: | Campinas, SP. |
| Institution: | Universidade Estadual de Campinas (UNICAMP). Instituto de Química |
| Defense date: | 2006-02-22 |
| Examining board members: |
Luiz Carlos Dias;
Simon John Garden;
Antonio Claudio Herrera Braga
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| Advisor: | Luiz Carlos Dias |
| Abstract | |
This work describes the stereoselective synthesis of the C29-C39 fragment of the immunosuppressant sanglifehrin A. Our strategy involved a diastereoselective boron-mediated 1,5-anti aldol reaction of methyl ketone 7.3 with chiral aldehyde 31.3(S) as the key step.j Methyl ketone 7.3 is viewed as arising from Weinreb amide 10.3. Key steps in this approach are Horner-Waddsworth-Emmons homologation, selective epoxidation and epoxide ring opening with a higher order cuprate. The Weireb amide 10.3 is available from a titanium mediated aldol reaction of N-propionyloxazolidinone 12.3 with metacrolein followed by a diastereoselective hydroboration. This approach to the C29-C39 fragment of sanglifehrin A requires 16 steps and produced the desired molecule in 18% overall yield. (AU) | |