ChemInform Abstract: Synthesis of 7-Substituted 5-Dethia-5-oxacephams via [2 + 2]Cycloaddition of Chlorosulfonyl Isocyanate to Sugar Vinyl Ethers.
Abstract
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ChemInform Abstract
[2+2]Cycloaddition of chlorosulfonyl isocyanate (V) to appropriate alkenyl ethers of protected α-D-xylofuranose [cf. (IV)] proceeds with high stereoselectivity to afford the respective azetidinones (VI). Subsequent transformations of adducts consisting in detritylation, tosylation and intramolecular alkylation of the nitrogen atom provides access to corresponding tetracyclic 5-oxacephams [cf. (VIII); 4 examples].
