The first stereocontrolled synthesis of 12-methyl-hexahydrobenzo[c]phenanthridine alkaloids |
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| Institution: | 1. School of Pharmacy, University of Wisconsin-Madison, Madison, WI 53705, United States;2. Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, United States;1. Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100, Gliwice, Poland;2. Biotechnology Centre of Silesian University of Technology, B. Krzywoustego 8, 44-100, Gliwice, Poland;3. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland |
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| Abstract: | 12-Methyl B/C hexahydrobenzoc]phenanthridines have been synthesized stereoselectively starting from chiral nonracemic 2-aryl-4-pentenoic acids prepared by asymmetric allylation of (+)-(S,S)-pseudoephedrine-based arylacetamide enolates. Subsequent transformations (Friedel–Crafts acylation, stereocontrolled reductive amination, Pictet–Spengler cyclization and PPA catalyzed cationic cyclization) led to the synthesis of enantiomerically enriched hexahydrobenzoc]phenanthridines in which the sequential formation of all the new stereogenic centres was controlled by the starting chiral acids. |
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