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Synthesis And Reductive Desulfurization Of Chiral Non-racemic Benzothienoindolizines. An Efficient Approach To A Novel Bioactive Tylophorine Alkaloid Analogue And 6-phenylindolizidine

P. Šafár̆, Jozefína Žúžiová, Mária Bobošíková, Štefan Marchalín, N. Prónayová, S. Comesse, A. Daïch
Published 2009 · Chemistry

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Abstract Enantiopure di- and tetrahydro[1]benzothieno[3,2- f ]indolizines 3 , 4 , 9 and the benzothieno analogue 5 of the bioactive alkaloid tylophorine 10 were synthesized easily from the readily available benzo[ b ]thiophene-3-carboxaldehyde 1 and ( S )-glutamic acid 2 in good overall yields. Applying a diastereoselective reductive desulfurization of benzo[ b ]thiophene 3 , 4 and 5 were readily converted into the enantiopure alcohols 11a–d, alcohols 11c,d and the target 6( R )-phenyl-8a( R )-indolizidine 6 (7 steps, 14%). During these reduction studies, the results obtained including the stereoinduction of the reaction are also discussed.
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