Rapid synthesis of the ervitsine alkaloid skeleton by a sequential RCM-Heck cyclization approach

被引：19

作者：

Bennasar, M. -Lluisa

Zulaica, Ester

Sole, Daniel

Alonso, Sandra

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

[2] Univ Barcelona, Inst Biomed IBUB, E-08028 Barcelona, Spain

来源：

SYNLETT | 2008年 / 05期

关键词：

indoles; annulation; metathesis; Heck reaction; alkaloids;

D O I：

10.1055/s-2008-1032102

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient approach to the bridged framework of the indole alkaloid ervitsine, featuring a ring-closing metathesis reaction from a 2,3-disubstituted indole followed by a vinyl halide Heck cyclization upon the resulting cycloheptene ring, is described.

引用

收藏

页码：667 / 670

页数：4

相关论文

共 36 条

[1]

[Anonymous], SCI SYNTHESIS

[2] A SYNTHETIC ROAD TO THE FOREST OF STRYCHNOS, ASPIDOSPERMA, SCHIZOZYGANE AND EBURNAMINE ALKALOIDS BY WAY OF THE NOVEL PHOTO-ISOMERIZATION [J].

BAN, Y ;

YOSHIDA, K ;

GOTO, J ;

OISHI, T ;

TAKEDA, E .

TETRAHEDRON, 1983, 39 (22) :3657-3668

[3] Facile synthesis of azocino[4,3-b]indoles by ring-closing metathesis [J].

Bennasar, M. -Lluisa ;

Zulaica, Ester ;

Sole, Daniel ;

Alonso, Sandra .

TETRAHEDRON, 2007, 63 (04) :861-866

[4] Preparation of RCM substrates for azepinoindole synthesis:: reductive amination versus tetrahydro-γ-carboline formation [J].

Bennasar, ML ;

Zulaica, E ;

Alonso, S .

TETRAHEDRON LETTERS, 2005, 46 (46) :7881-7884

[5] A synthetic entry to 2,3-fused ring indole derivatives by ring-closing metathesis reactions [J].

Bennasar, ML ;

Zulaica, E ;

Tummers, S .

TETRAHEDRON LETTERS, 2004, 45 (33) :6283-6285

[6] 1ST TOTAL SYNTHESIS OF THE INDOLE ALKALOID ERVITSINE - A STRAIGHTFORWARD, BIOMIMETIC APPROACH [J].

BENNASAR, ML ;

VIDAL, B ;

BOSCH, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) :5340-5341

[7] Biomimetic total synthesis of ervitsine and indole alkaloids of the ervatamine group via 1,4-dihydropyridines [J].

Bennasar, ML ;

Vidal, B ;

Bosch, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (11) :3597-3609

[8]

Benner M, 2003, TRENDS FOOD SCI TECH, V14, P469, DOI 10.1016/S0924-2244(03)00154-7

[9] A novel route to the geissoschizine skeleton: The influence of ligands on the diastereoselectivity of the Heck cyclization [J].

Birman, VB ;

Rawal, VH .

TETRAHEDRON LETTERS, 1998, 39 (40) :7219-7222

[10] A general, stereocontrolled route to the geissoschizine family of alkaloids. Concise synthesis of the apogeissoschizine skeleton [J].

Birman, VB ;

Rawal, VH .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9146-9147

← 1 2 3 4 →