New strategies to symmetric and unsymmetric cyclic sulfamide analogs of DMP 323: a ‘sulfur linchpin’/RCM approach

The synthesis of 7-membered cyclic sulfamides utilizing the RCM reaction is described herein. Two major synthetic strategies that expand the scope and utility of our previously reported sulfamide and sulfamoyl carbamate chemistry are employed. Both Mitsunobu alkylation and simple alkylation of core sulfamides and sulfamoyl carbamates coupled with RCM are used to efficiently install lipophilic groups into the P1/P1′ and P2/P2′ periphery of the cyclic sulfamides. Overall, the routes described are applicable to the synthesis of a variety of cyclic 7-membered sulfamides.