DIASTEREOCONTROLLED AND ENANTIOCONTROLLED SYNTHESIS OF (-)-ALLOSEDAMINE VIA CYCLOADDITION OF A CHIRAL NITRONE

被引：45

作者：

OPPOLZER, W

DEERBERG, J

TAMURA, O

机构：

[1] Département de Chimie Organique, Université de Genève, Genève

来源：

HELVETICA CHIMICA ACTA | 1994年 / 77卷 / 02期

关键词：

D O I：

10.1002/hlca.19940770217

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The piperidine alkaloid (-)-allosedamine (1) has been synthesized, in 21% overall yield, in nine steps starting from the formyl-ester 4. The synthesis features the reaction cascade 7 --> 3 --> 2. involving asymmetric electrophilic enolate hydroxyamination, hydroxylamine/aldehyde condensation, and nitrone/styrene cycloaddition, as well as the reductive N/O cleavage-decyanation 12 --> 1.

引用

收藏

页码：554 / 560

页数：7

相关论文

共 40 条

[1] CYCLOADDITIONS .33. STEREOSPECIFIC SYNTHESIS AND STEREOCHEMICAL STRUCTURE CONFIRMATION OF DUMETORINE [J].

AMARASEKARA, AS ;

HASSNER, A .

TETRAHEDRON LETTERS, 1987, 28 (27) :3151-3154

[2] MANIPULATION OF THE CARBOXYL GROUPS OF ALPHA-AMINO-ACIDS AND PEPTIDES USING RADICAL CHEMISTRY BASED ON ESTERS OF N-HYDROXY-2-THIOPYRIDONE [J].

BARTON, DHR ;

HERVE, Y ;

POTIER, P ;

THIERRY, J .

TETRAHEDRON, 1988, 44 (17) :5479-5486

[3] SYNTHESIS OF ANATOXIN-A VIA INTRA-MOLECULAR CYCLIZATION OF IMINIUM SALTS [J].

BATES, HA ;

RAPOPORT, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (05) :1259-1265

[4]

BEYERMAN HC, 1959, RECL TRAV CHIM PAY B, V78, P43

[5]

BEYERMAN HC, 1956, RECL TRAV CHIM PAY B, V75, P63

[6]

BOSONE E, 1983, SYNTHESIS-STUTTGART, P942

[7]

CAMPAGNA F, 1977, TETRAHEDRON LETT, P1813

[8] SYNTHESIS OF TRANS-2,6-DIALKYLPIPERIDINES BY 1,3-CYCLOADDITION OF ALKENES TO 2-ALKYL-2,3,4,5-TETRAHYDROPYRIDINE OXIDES [J].

CARRUTHERS, W ;

WILLIAMS, MJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (16) :1287-1288

[9] NITRONE CYCLOADDITIONS - SYNTHESIS OF (+/-)-ANDRACHAMINE [J].

CARRUTHERS, W ;

COGGINS, P ;

WESTON, JB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (08) :2323-2327

[10]

Confalone P. N., 1988, ORG REACTIONS, V36, P1

← 1 2 3 4 →