IMINOPHOSPHORANE-MEDIATED IMIDAZOLE RING FORMATION - A NEW AND GENERAL ENTRY TO APLYSINOPSIN-TYPE ALKALOIDS OF MARINE ORIGIN

被引：63

作者：

MOLINA, P

ALMENDROS, P

FRESNEDA, PM

机构：

[1] Departamento de Química Orgánica, Facultad de Química, E-30071 Murcia, Campus de Espinardo

来源：

TETRAHEDRON | 1994年 / 50卷 / 07期

关键词：

D O I：

10.1016/S0040-4020(01)85082-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aza Wittig-type reactions of iminophosphoranes 21, derived from ethyl alpha-azido-beta-(3-indolyl)propenoates and triphenylphosphine, with methyl isocyanate, carbon dioxide or carbon disulfide provide the corresponding heterocumulenes 22, 25 and 28 which undergo cyclization by the action of nitrogenous reagents completing the assemblage of the framework of aplysinopsin. Further deprotection leads to naturally occurring aplysinopsin analogues.

引用

页码：2241 / 2254

页数：14

共 15 条

[1]

Baker J.T., 1981, NATURAL PRODUCTS MED, P299

[2]

DALKAFUOKI A, 1991, TETRAHEDRON LETT, P5325

[3] STRUCTURE AND SYNTHESIS OF A NEW BROMOINDOLE FROM A MARINE SPONGE [J].