Highly diastereoselective approach to novel phenylindolizidinols via benzothieno analogues of tylophorine based on reductive desulfurization of benzo[ b]thiophene

Chiral tetra- and hexahydro[1]benzothieno[2,3- f]indolizines 3– 5, 9, and 11 were synthesized easily from benzo[ b]thiophene-2-carboxaldehyde ( 1) and ( S)-glutamic acid ( 2) in good overall yields and both high enantio- and diastereomeric purities. Applying a diastereoselective reductive desulfuriz...

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Published inTetrahedron: asymmetry Vol. 20; no. 5; pp. 626 - 634
Main Authors Safar, Peter, Zuziova, Jozefina, Marchalin, Stefan, Tothova, Eva, Pronayova, Nadezda, Svorc, Lubomir, Vrabel, Viktor, Daich, Adam
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.03.2009
Elsevier
Subjects
Catalysis
Chemical Sciences
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Medicinal Chemistry
Organic chemistry
Physical Sciences
Science & Technology
SWAINSONINE ANALOGS
THERAPEUTIC APPLICATIONS
QUINOLIZIDINE ALKALOIDS
MANNOSIDASE INHIBITORY ACTIVITY
BIOLOGICAL-ACTIVITY
EXPEDIENT SYNTHESIS
INDOLIZIDINE
NATURAL OCCURRENCE
GLYCOSIDASE INHIBITORS
AROMATIC-COMPOUNDS
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Summary:Chiral tetra- and hexahydro[1]benzothieno[2,3- f]indolizines 3– 5, 9, and 11 were synthesized easily from benzo[ b]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 benzo[ b]thiophene followed by lactam reduction, epimeric alcohols 4a and 4b were readily converted into (7 R or S,8a S)-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.
ISSN:0957-4166
1362-511X
0957-4166
DOI:10.1016/j.tetasy.2009.02.042