cis-trans Isomerization of silybins A and B

被引：15
作者：
Novotna, Michaela [1 ]
Gazak, Radek [1 ,2 ]
Biedermann, David [1 ]
Di Meo, Florent [3 ]
Marhol, Petr [1 ]
Kuzma, Marek [1 ]
Bednarova, Lucie [4 ]
Fuksova, Katerina [1 ]
Trouillas, Patrick [3 ,5 ,6 ]
Kren, Vladimir [1 ]
机构：
[1] Vvi AS CR, Inst Microbiol, CZ-14220 Prague 4, Czech Republic
[2] Charles Univ Prague, Fac Sci, Dept Biochem, CZ-12840 Prague 2, Czech Republic
[3] Univ Limoges, Fac Pharm, INSERM, UMR S850, F-87025 Limoges, France
[4] Vvi AS CR, Inst Organ Chem & Biochem, CZ-16610 Prague 6, Czech Republic
[5] Univ Olomouc, Dept Phys Chem, CZ-77146 Olomouc, Czech Republic
[6] Univ Mons, Lab Chim Mat Nouveaux, B-7000 Mons, Belgium
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 10卷
关键词：
2,3-cis-silybin; 10,11-cis-silybin; isomerization; silibinin; silybin; silymarin; ABSOLUTE-CONFIGURATION; CIRCULAR-DICHROISM; ASYMMETRIC-SYNTHESIS; MARIANUM; DIASTEREOISOMERS; FLAVONOLIGNANS; CONSTITUENTS; ISOSILYBIN; SEPARATION; NEOLIGNANS;
D O I：
10.3762/bjoc.10.105
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Methods were developed and optimized for the preparation of the 2,3-cis- and the 10,11-cis-isomers of silybin by the Lewis acid catalyzed (BF3 center dot OEt2) isomerization of silybins A (1a) and B (1b) (trans-isomers). The absolute configuration of all optically pure compounds was determined by using NMR and comparing their electronic circular dichroism data with model compounds of known absolute configurations. Mechanisms for cis-trans-isomerization of silybin are proposed and supported by quantum mechanical calculations.
引用
收藏
页码：1047 / 1063
页数：17
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