CONVERSION OF DELTA-(SULFONYL)AMINO-ALPHA-EPOXY KETONES TO BICYCLIC KETOPYRROLES VIA INTRAMOLECULAR CONJUGATE-ADDITION TO AZOENE INTERMEDIATES - SYNTHESIS OF THE BICYCLIC KETOPYRROLE CORE OF THE 1-AZAFULVENE ROSEOPHILIN

Authors
KIM SH FUCHS PL
Citation
Sh. Kim et Pl. Fuchs, CONVERSION OF DELTA-(SULFONYL)AMINO-ALPHA-EPOXY KETONES TO BICYCLIC KETOPYRROLES VIA INTRAMOLECULAR CONJUGATE-ADDITION TO AZOENE INTERMEDIATES - SYNTHESIS OF THE BICYCLIC KETOPYRROLE CORE OF THE 1-AZAFULVENE ROSEOPHILIN, Tetrahedron letters, 37(15), 1996, pp. 2545-2548
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
15
Year of publication
1996
Pages
2545 - 2548
Database
ISI
SICI code
0040-4039(1996)37:15<2545:CODKTB>2.0.ZU;2-S
Abstract
Reaction of delta-(sulfonyl)amino-alpha-epoxy ketones with dimethylhyd razine results in cyclization to pyrrolidine-fused beta-hydroxy dimeth ylhydrazones. elimination affords dihydropyrroles which can be convert ed to sulfonyl-protected ketopyrroles via oxidation with NIS; alternat ively, treatment with DBU affords N-H bearing ketopyrroles. Copyright (C) 1996 Elsevier Science Ltd