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Preparation of novel tricyclic diazo carbapenems: Application of inverse electron demand Diels-Alder reactions of 3,6-bis(methylthio)-1,2,4,5-tetrazine

✍ Scribed by Subas M. Sakya; Timothy W. Strohmeyer; Stanley A. Lang; Yang-I Lin

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
188 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

The syntheses of novel lricyclic diazo carbapenem precursor 17, and the deprotected carbapenems 2 and 3 are described. The construction of the tricyclic carbapenem was accomplished by an intramolecular nucleophilic substitution of the diazine sulfone 16 which was obtained from an inverse electron demand Dials-Alder reaction of the alkynyl azetidinone 13 with 3,6-bis(methylthio)-1,2,4,5-tetrazine (4).

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