Gentrymine B, an N-quaternary Ancistrocladus alkaloid:: Stereoanalysis, synthesis, and biomimetic formation from gentrymine A

被引：14

作者：

Bringmann, G ^{[1
]}

Ochse, M ^{[1
]}

Michel, M ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

TETRAHEDRON | 2000年 / 56卷 / 04期

关键词：

gentrymine B; Ancistrocladus korupensis; biomimetic synthesis; isoquinoline alkaloids;

D O I：

10.1016/S0040-4020(99)01054-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the N-quaternary isoquinoline alkaloid gentrymine B (1) and of its unnatural enantiomer as well as its oxidative degradation is described. A further proof of stereostructure and hints at the biosynthetic origin of the unusual S,S-configuration in gentrymine B (1) were obtained by an additional biomimetic synthesis of 1 from the related-but 1R-configured-natural product gentrymine A (2), by N-methylation and subsequent spontaneous epimerization at C-l. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：581 / 585

页数：5

共 13 条

[1]

[Anonymous], INTRO ALKALOIDS

[2] ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS [J].

BOYD, MR ;

HALLOCK, YF ;

MANFREDI, KP ;

BLUNT, JW ;

MCMAHON, JB ;

BUCKHEIT, RW ;

BRINGMANN, G ;

SCHAFFER, M ;

CRAGG, GM ;

THOMAS, DW ;

JATO, JG ;

CARDELLINA, JH .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1740-1745

[3] N,N-dimethyldioncophyllinium A iodide: Synthesis, stereoanalysis, and antimalarial activity of the first N-quaternary naphthylisoquinolinium salt [J].

Bringmann, G ;

Ochse, M ;

Schaffer, M ;

God, R ;

Walter, R ;

Francois, G .

PLANTA MEDICA, 1997, 63 (06) :544-547

[4]

BRINGMANN G, 1993, LIEBIGS ANN CHEM, P877

[5] An improved degradation procedure for determination of the absolute configuration in chiral isoquinoline and beta-carboline derivatives [J].

Bringmann, G ;

God, R ;

Schaffer, M .

PHYTOCHEMISTRY, 1996, 43 (06) :1393-1403

[6]

BRINGMANN G, UNPUB J ORG CHEM

[7]

Bringmann G., 1995, ALKALOIDS, V46, P127

[8]

DALTON DR, 1979, ALKALOIDS

[9]

DEEKNAMKUL W, 1992, PHYTOCHEMISTRY, V31, P813, DOI 10.1016/0031-9422(92)80020-F

[10] KORUPENSAMINES-A-D, NOVEL ANTIMALARIAL ALKALOIDS FROM ANCISTROCLADUS-KORUPENSIS [J].

HALLOCK, YF ;

MANFREDI, KP ;

BLUNT, JW ;

CARDELLINA, JH ;

SCHAFFER, M ;

GULDEN, KP ;

BRINGMANN, G ;

LEE, AY ;

CLARDY, J ;

FRANCOIS, G ;

BOYD, MR .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6349-6355

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