Synthesis of (+/-)-Carbocyclic Analogue of Spirohydantoin Nucleoside

Article abstract of DOI:10.1016/0040-4020(95)00162-2

Synthesis of (+/-)-carbocyclic spirohydantoin derivatives of (+)-hydantocidin is described.The pivotal step in the synthesis is spirohydantoin ring construction from cyclopentanone 9.Using the Bucherer-Bergs condition predominately gave the epi-carbocyclic analogue 10, whereas the alternative spiroring formation method through α-aminonitrile 13 provided the carbocyclic analogue 2 after deprotection.