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Synthesis of 2,6-disubstituted piperidine alkaloids from ladybird beetles Calvia 10-guttata and Calvia 14-guttata |
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| Authors: | Peter Kubizna Jozef Ko?íšek |
| Institution: | a Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovakia c Department of Analytical Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovakia b Department of Physical Chemistry, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovakia |
| Abstract: | Optically pure (+)-calvine, (+)-2-epicalvine, (2S,6S)-(6-pentylpiperidin-2-yl)acetic acid methyl ester and (2R,6S)-(6-pentylpiperidin-2-yl)acetic acid methyl ester, four piperidine alkaloids isolated from ladybird beetles of the genus Calvia (Coccinellidae), were synthesised from a common precursor using cyclisative Pd(II)/Cu(II)-catalysed carboamination-(methoxy)carbonylation tandem reaction of alkenylamines as a key step. The first single-crystal X-ray analysis of (+)-calvine confirmed its proposed absolute configuration to be (2S,6S) corresponding to that of natural product. |
| Keywords: | Palladium Carbonylation Amino alcohols Heterogeneous catalysis Natural products |
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