Synthesis of naturally occurring o-heterocyclic compounds of biological activity

Verfasser / Beitragende:
[Sándor Antus, Katalin Gulácsi, László Juhász, Loránd Kiss, Tibor Kurtán]
Ort, Verlag, Jahr:
2004
Enthalten in:
Pure and Applied Chemistry, 76/5(2004-01-01), 1025-1032
Format:
Artikel (online)
ID: 378911252
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024 7 0 |a 10.1351/pac200476051025  |2 doi 
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245 0 0 |a Synthesis of naturally occurring o-heterocyclic compounds of biological activity  |h [Elektronische Daten]  |c [Sándor Antus, Katalin Gulácsi, László Juhász, Loránd Kiss, Tibor Kurtán] 
520 3 |a The total synthesis of (−)-cabenegrin A-I was achieved via (−)-6aR,11aR maackiain, which was obtained by optical resolution of racemic maackiain using S-(−)-alpha-methylbenzyl isocyanate. The synthesis of rac-maackiain was performed both with the Heck oxyarylation of 7-benzyloxy-2H-chromene and the BF3OEt2 mediated ring closure of isoflavan-4-ol derivatives, the latter of which provided much higher yields. The first enantioselective synthesis of trans-6aS,11aR-pterocarpan and its conversion to cis-6aS,11aS -ptarocarpan was also presented starting from racemic 2'-benzyloxyflavanone. Their stereochemistry was deduced by circular dichroism (CD) as well as by X-ray analysis of the ketal intermediate. 
540 |a © 2013 Walter de Gruyter GmbH, Berlin/Boston 
700 1 |a Antus  |D Sándor  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
700 1 |a Gulácsi  |D Katalin  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
700 1 |a Juhász  |D László  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
700 1 |a Kiss  |D Loránd  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
700 1 |a Kurtán  |D Tibor  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
773 0 |t Pure and Applied Chemistry  |d De Gruyter  |g 76/5(2004-01-01), 1025-1032  |x 0033-4545  |q 76:5<1025  |1 2004  |2 76  |o pac 
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950 |B NATIONALLICENCE  |P 700  |E 1-  |a Antus  |D Sándor  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Gulácsi  |D Katalin  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Juhász  |D László  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Kiss  |D Loránd  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Kurtán  |D Tibor  |u Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Pure and Applied Chemistry  |d De Gruyter  |g 76/5(2004-01-01), 1025-1032  |x 0033-4545  |q 76:5<1025  |1 2004  |2 76  |o pac 
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