Open AccessSynthesis of tricyclic azetidinones by intramolecular free radical cyclization
Author(s) -
George Just,
Guerino Sacripante
Publication year - 1987
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v87-017
Subject(s) - chemistry , tributyltin hydride , tricyclic , radical cyclization , intramolecular force , free radical reaction , hydride , medicinal chemistry , stereochemistry , radical , organic chemistry , hydrogen
The synthesis of strained tricyclic azetidinones was achieved by free radical cyclization of N-substituted azetidinones involving a tributyltin hydride/AIBN mediated chain reaction. The 5-exo cyclization led to benzo carbapenems 10, 12, and 13, which were relatively unstable in solution. The 6-exo mode, however, afforded stable benzo carbacephems 20, 22, 24, and 25.
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