Ancisheynine, the first N,C-coupled naphthylisoquinoline alkaloid:: Total synthesis and stereochemical analysis

被引：60

作者：

Bringmann, G ^{[1
]}

Guider, T ^{[1
]}

Reichert, M ^{[1
]}

Meyer, F ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 06期

关键词：

D O I：

10.1021/ol052946p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of an N,C-coupled naphthylisoquinoline alkaloid-ancisheynine-was achieved by condensing a monocyclic diketone or the respective benzopyrylium salt with an aminonaphthalene. The presence of a rotationally hindered axis in ancisheynine was demonstrated by resolution of its two atropo-enantiomers by HPLC on a chiral phase with LC-CD coupling. The assignment of their axial configurations succeeded by quantum chemical CD calculations.

引用

页码：1037 / 1040

页数：4

共 33 条

[1]

ALVAREZ M, 2005, SCIENCE SYNTHESIS HO

[2] New chiral isoquinolinium salt derivatives from chiral primary amines via Zincke reaction [J].

Barbier, D ;

Marazano, C ;

Das, BC ;

Potier, P .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9596-9598

[3] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[4] ACETOGENIN ISOQUINOLINE ALKALOIDS .10. ONE POT PREPARATION OF "1,3-DIMETHYLTETRAHYDROISOQUINOLINES FROM THEIR BIOSYNTHETIC DIKETO PRECURSORS [J].

BRINGMANN, G ;

JANSEN, JR .

HETEROCYCLES, 1986, 24 (09) :2407-2410

[5]

Bringmann G, 1997, J LABELLED COMPD RAD, V39, P29, DOI 10.1002/(SICI)1099-1344(199701)39:1<29::AID-JLCR936>3.0.CO

[6]

2-Y

[7] ent-dioncophylleine A and related dehydrogenated naphthylisoquinoline alkaloids, the first Asian dioncophyllaceae-type alkaloids, from the "new" plant species Ancistrocladus benomensis [J].

Bringmann, G ;

Dreyer, M ;

Kopff, H ;

Rischer, H ;

Wohlfarth, M ;

Hadi, HA ;

Brun, R ;

Meimberg, H ;

Heubl, G .

JOURNAL OF NATURAL PRODUCTS, 2005, 68 (05) :686-690

[8] Stereochemistry of isoplagiochin C, a macrocyclic bisbibenzyl from liverworts [J].

Bringmann, G ;

Mühlbacher, J ;

Reichert, M ;

Dreyer, M ;

Kolz, J ;

Speicher, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9283-9290

[9]

Bringmann G, 2001, PROG CH ORG NAT PROD, V82, P1

[10] Stress-related polyketide metabolism of dioncophyllaceae and ancistrocladaceae [J].

Bringmann, G ;

Feineis, D .

JOURNAL OF EXPERIMENTAL BOTANY, 2001, 52 (363) :2015-2022

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