Highly diastereoselective approach to novel phenylindolizidinols via benzothieno analogues of tylophorine based on reductive desulfurization of benzo[b]thiophene |
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| Authors: | Peter ?afá? Jozefína ?ú?iová ?tefan Marchalín Eva Tóthová Nade?da Prónayová ?ubomír ?vorc Viktor Vrábel Adam Daïch |
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| Institution: | 1. Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovak Republic;2. Central Laboratories, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovak Republic;3. Department of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovak Republic;4. URCOM, EA 3221, UFRST, CNRS INC3M FR-3038 Université du Havre, 25 rue Philippe Lebon, BP: 540, F-76058 Le Havre Cedex, France |
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| Abstract: | Chiral tetra- and hexahydro1]benzothieno2,3-f]indolizines 3–5, 9, and 11 were synthesized easily from benzob]thiophene-2-carboxaldehyde (1) and (S)-glutamic acid (2) in good overall yields and both high enantio- and diastereomeric purities. Applying a diastereoselective reductive desulfurization of benzob]thiophene followed by lactam reduction, epimeric alcohols 4a and 4b were readily converted into (7R or S,8aS)-phenylindolizidinols 6a,c. During these studies, the reduction of benzothienoindolizines 3–5, 9, 11, and 12, was investigated and the results obtained are also discussed. |
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