PREPARATION OF NOVEL TRICYCLIC DIAZO CARBAPENEMS - APPLICATION OF INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 3,6-BIS(METHYLTHIO)-1,2,4,5-TETRAZINE

Authors
SAKYA SM STROHMEYER TW LANG SA LIN YI
Citation
Sm. Sakya et al., PREPARATION OF NOVEL TRICYCLIC DIAZO CARBAPENEMS - APPLICATION OF INVERSE ELECTRON DEMAND DIELS-ALDER REACTIONS OF 3,6-BIS(METHYLTHIO)-1,2,4,5-TETRAZINE, Tetrahedron letters, 38(34), 1997, pp. 5913-5916
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
34
Year of publication
1997
Pages
5913 - 5916
Database
ISI
SICI code
0040-4039(1997)38:34<5913:PONTDC>2.0.ZU;2-N
Abstract
The syntheses of novel tricyclic diazo carbapenem precursor 17, and th e deprotected carbapenems 2 and 3 are described. The construction of t he tricyclic carbapenem was accomplished by an intramolecular nucleoph ilic substitution of the diazine sulfone 16 which was obtained from an inverse electron demand Diels-Alder reaction of the alkynyl azetidino ne 13 with 3,6-bis(methylthio)-1,2,4,5-tetrazine (4).