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- Title
Epimeric Isopavine N-Oxides from Roemeria refracta.
- Authors
Gözler, Belkis; Ali Önür, Mustafa; Bilir, Serap; Hesse, Manfred
- Abstract
Roemeria refracta DC. (Papaveraceae) of Turkish origin yielded two novel epimeric N-oxides, (−)-(5 R, 11 S,14 R)-reframidine N-oxide ( = (−)-(5 R, 11 S,14 R)-11,12-dihydro-14-methyl-11,5-(iminomethano)-5 H -cyclohepta[1, 2- f: 4, 5- f′]bis[1,3]benzodioxole 14-oxide; 1) and (−)-(5 R, 11 S, 14 S)-reframidine N-oxide ( = (−)-(5 R, 11 S, 14 S)-11, 12-dihydro-14-methyl-11, 5-(iminomethano)-5 H-cyclohepta[1, 2- f:4, 5- f′]bis[1, 3]benzodioxole 14-oxide; 2). The isolated (−)-roelactamine ( = (−)-11, 12-dihydro-14-methyl-11, 5-(iminomethano)-5 H-cyclohepta[1, 2- f:4, 5- f′]bis[1, 3]benzodioxol-15-one, 4) is the first natural isopavinoid incorporating a lactam group. The epimeric (−)-15-(2-oxopropyl)reframidines ( = (−)-1-[11, 12-dihydro-14-methyl-11, 5-(iminomethano)-5 H-cyclohepta[1, 2- f:4, 5- f′]bis[1, 3]benzodioxol-15-y1]propan-2-ones; 5/6) and the epimeric (−)-ethyl (reframidin-15-yl)acetates ( = (−)-ethyl [11, 12-dihydro-14-methyl-11, 5-(iminomethano)-5 H-cyclohepta[1, 2- f:4, 5- f′]bis[1, 3]benzodioxol-15-y1]acetates; 7/8) are probably artifacts. (±)-Coclaurine ( 9), (±)- N-methylcoclaurine ( 10), (−)-roemeridine ( 11), and N-feruloyltyramine ( 12) are also isolated from R. refracta together with the previously reported bases. Specific 13C-NMR assignments are reported for the first time for the isopavines.
- Publication
Helvetica Chimica Acta, 1992, Vol 75, Issue 1, p260
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19920750121