caa a22 4500 378911252 CHVBK 20180305123542.0 cr unu---uuuuu 161128e20040101xx s 000 0 eng 10.1351/pac200476051025 doi (NATIONALLICENCE)gruyter-10.1351/pac200476051025 Synthesis of naturally occurring o-heterocyclic compounds of biological activity [Elektronische Daten] [Sándor Antus, Katalin Gulácsi, László Juhász, Loránd Kiss, Tibor Kurtán] 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. © 2013 Walter de Gruyter GmbH, Berlin/Boston Antus Sándor Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut Gulácsi Katalin Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut Juhász László Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut Kiss Loránd Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut Kurtán Tibor Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut Pure and Applied Chemistry De Gruyter 76/5(2004-01-01), 1025-1032 0033-4545 76:5<1025 2004 76 pac https://doi.org/10.1351/pac200476051025 text/html Onlinezugriff via DOI 1 research article jats NATIONALLICENCE 856 40 https://doi.org/10.1351/pac200476051025 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Antus Sándor Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut NATIONALLICENCE 700 1- Gulácsi Katalin Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut NATIONALLICENCE 700 1- Juhász László Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut NATIONALLICENCE 700 1- Kiss Loránd Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut NATIONALLICENCE 700 1- Kurtán Tibor Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, P.O. Box 20, Hungary aut NATIONALLICENCE 773 0- Pure and Applied Chemistry De Gruyter 76/5(2004-01-01), 1025-1032 0033-4545 76:5<1025 2004 76 pac CC0 http://creativecommons.org/publicdomain/zero/1.0 nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-gruyter