Application of the Rh(II) cyclization/cycloaddition cascade for the total synthesis of (±)-aspidophytine

被引：124

作者：

Mejia-Oneto, Jose M. ^{[1
]}

Padwa, Albert ^{[1
]}

机构：

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 15期

关键词：

D O I：

10.1021/ol061137i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new strategy for the synthesis of (+/-)-aspidophytine has been developed and is based on a Rh(II)-catalyzed cyclization/dipolar cycloaddition sequence. The resulting [3+2]-cycloadduct undergoes an efficient Lewis acid mediated cascade that rapidly provides the complete skeleton of aspidophytine. The synthesis also features a mild decarbomethoxylation reaction.

引用

收藏

页码：3275 / 3278

页数：4

相关论文

共 70 条

[21] A NOVEL TIN-MEDIATED INDOLE SYNTHESIS [J].

FUKUYAMA, T ;

CHEN, XQ ;

PENG, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :3127-3128

[22] INDOLE-2,3-QUINODIMETHAN ROUTE TO ASPIDOSPERMA ALKALOIDS - SYNTHESIS OF DL-ASPIDOSPERMIDINE [J].

GALLAGHER, T ;

MAGNUS, P ;

HUFFMAN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (04) :1140-1141

[23] Synthesis of an aspidosperma alkaloid precursor:: synthesis of (+)-aspidospermidine [J].

Gnecco, D ;

Vázquez, E ;

Galindo, A ;

Terán, JL ;

Orea, L ;

Bernès, S ;

Enríquez, RG .

ARKIVOC, 2003, :185-192

[24] Enantioselective total synthesis of aspidophytine [J].

He, F ;

Bo, YX ;

Altom, JD ;

Corey, EJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6771-6772

[25]

Herbert R B, 1994, CHEM HETEROCYCLIC 4, V25

[26]

HERBERT RB, 1994, MONOTERPENOID INDOLE, V25, pCH1

[27]

HERBERT RB, 1994, MONOTERPENOID INDO S, V25

[28] Regiocontrol in an intramolecular Schmidt reaction:: Total synthesis of (+)-aspidospermidine [J].

Iyengar, R ;

Schildknegt, K ;

Aubé, J .

ORGANIC LETTERS, 2000, 2 (11) :1625-1627

[29] Efficient total syntheses of (±)-vincadifformine and (-)-tabersonine [J].

Kobayashi, S ;

Peng, G ;

Fukuyama, T .

TETRAHEDRON LETTERS, 1999, 40 (08) :1519-1522

[30]

Kobayashi S, 2000, SYNLETT, P883

← 1 2 3 4 5 6 7 →