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

页码：1047 / 1063

页数：17

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