SYNTHESIS OF PYRROLO-CASTANOSPERMINE ANALOGS - A NOVEL FLUORIDE-ION INDUCED REARRANGEMENT OF A 3-TRIALKYLSILYL SUBSTITUTED DIHYDRO-2H-1,2-OXAZINE TO A PYRROLE

被引：27

作者：

KEFALAS, P ^{[1
]}

GRIERSON, DS ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 22期

关键词：

D O I：

10.1016/S0040-4039(00)73634-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hetero Diels-Alder reaction of diene 10, obtained in one step from aldehyde 4, with nitroso dienophile 6 produced the dihydro-2H-1,2-oxazines 12. Treatment of the tosylates 13 derived from 12 with TBAF induced a ring contraction process leading directly to pyrrole 16. Cyclization of this intermediate furnished the pyrrolo-castanospermine derivative 17.

引用

页码：3555 / 3558

页数：4

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