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

Authors
KEFALAS P GRIERSON DS
Citation
P. Kefalas et Ds. Grierson, SYNTHESIS OF PYRROLO-CASTANOSPERMINE ANALOGS - A NOVEL FLUORIDE-ION INDUCED REARRANGEMENT OF A 3-TRIALKYLSILYL SUBSTITUTED DIHYDRO-2H-1,2-OXAZINE TO A PYRROLE, Tetrahedron letters, 34(22), 1993, pp. 3555-3558
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
22
Year of publication
1993
Pages
3555 - 3558
Database
ISI
SICI code
0040-4039(1993)34:22<3555:SOPA-A>2.0.ZU;2-3
Abstract
Hetero Diels-Alder reaction of diene 10, obtained in one step from ald ehyde 4, with nitroso dienophile 6 produced the dihydro-2H-1,2-oxazine s 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.