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An alternative approach to the synthesis of the carbapenam ring system. Allenes as acceptor-donor reagents in 3 + 2 annelations

✍ Scribed by Harold Mastalerz; Vivianne Vinet


Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
263 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis


l,l-Dichloro-3-methylsulfonyl-3-methylthio-l,2-propadier~e, generated in btiU under basic conditions, reacted with a 4-iodomethylazetidinone to give a carbapenam. Subsequent efforts to convert this material to a A-Z-carbapenem by rearrangement of an allylic sulfoxide led instead to the formation of a novel A-1-carbapenem.

Recently several groups I" have described syntheses of the carbapenam ring system via