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An easy and stereoselective synthesis of N-Boc-dolaproine via the Baylis-Hillman reaction |
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| Authors: | Wanda P Almeida Fernando Coelho |
| Institution: | a CREUPI, Esp?́rito Santo do Pinhal, 13990-000-SP, Brazil b Curso de Pós-Graduação em Biologia Celular e Estrutural, IB/Unicamp, PO Box 6109, 13084-971-Campinas-SP, Brazil c DQO/IQ, UNICAMP, PO Box 6154, 13083-970-Campinas-SP, Brazil |
| Abstract: | In this communication we report a stereoselective total synthesis of N-Boc-dolaproine (Dap), an amino acid residue of the antineoplastic pentapeptide Dolastatin 10. Our strategy is based on a Baylis-Hillman reaction between N-Boc-prolinal and methyl acrylate, followed by a diastereoselective double bond hydrogenation and hydrolysis of the ester function. |
| Keywords: | dolaproine Baylis-Hillman hydrogenation amino aldehydes |
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