Studies on the total synthesis of sanglifehrin A: stereoselective synthesis of the C(29)-C(39) fragment |
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Authors: | Luiz C. Dias Airton G. Salles Jr. |
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Affiliation: | Instituto de Química, Universidade Estadual de Campinas, UNICAMP, C.P. 6154, 13084-971 Campinas, SP, Brazil |
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Abstract: | A highly stereoselective synthesis of the C(29)-C(39) fragment of the potent immunosuppressant sanglifehrin A has been accomplished by a sequence involving 16 steps (18% overall yield) from N-propionyloxazolidinone 9. Key steps are a diastereoselective hydroboration, and a diastereoselective epoxidation of an allylic alcohol followed by a 1,5-anti boron-mediated aldol reaction of methyl ketone 4 with chiral aldehyde 5. |
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Keywords: | Immunosuppressant 1,5-Anti aldol 1,5-Asymmetric induction |
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