SYNTHESIS OF ALPHA,BETA-UNSATURATED SPIROLACTAMS BY INTRAMOLECULAR CYCLIZATION OF ENDOCYCLIC N-ACYLIMINIUM IONS

Authors
MARTIN MJ BERMEJO F
Citation
Mj. Martin et F. Bermejo, SYNTHESIS OF ALPHA,BETA-UNSATURATED SPIROLACTAMS BY INTRAMOLECULAR CYCLIZATION OF ENDOCYCLIC N-ACYLIMINIUM IONS, Tetrahedron letters, 36(42), 1995, pp. 7705-7708
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
42
Year of publication
1995
Pages
7705 - 7708
Database
ISI
SICI code
0040-4039(1995)36:42<7705:SOASBI>2.0.ZU;2-U
Abstract
The synthesis of 3-methyl-3-en-1,6-diazaspiro-[4.5]decane-2,7-dione (1 8), the spiro moiety of (+/-)-pandamarine has been achieved try oxidat ive cyclization of the (Z) and (E) isomers of rboxamido-butylidene)-3- methyl-3-en-pyrrolin-2-one (15a) and(15b). The stereoselectivity exhib ited in the intramolecular cyclization by both butylidene precursors h as also been discussed.