A general, convergent strategy for the construction of indolizidine alkaloids: total syntheses of (-)-indolizidine 223AB and alkaloid (-)-205B |
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Authors: | Smith Amos B Kim Dae-Shik |
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Institution: | Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, PA 19104, USA. smithab@sas.upenn.edu |
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Abstract: | N-Toluenesulfonyl aziridines comprise effective second electrophiles in the solvent controlled three-component linchpin union of silyl dithianes for the stereocontrolled convergent elaboration of protected 1,5-amino alcohols. This tactic, in conjunction with a one-flask sequential cyclization, constitutes an effective general strategy for the construction of indolizidine and related alkaloids, illustrated here with the total syntheses of (-)-indolizidine 223AB (1) and alkaloid (-)-205B (2). |
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