Revision of the structure of haliclorensin to (S)-7-methyl-1,5-diazacyclotetradecane and confirmation of the new structure by synthesis

A reinvestigation of the marine alkaloid haliclorensin led to a revision of the proposed structure to 7-methyl-1,5-diazacyclotetradecane. The new structure was confirmed by total synthesis of both optical forms. According to chiroptical measurements and GC–MS investigations, natural haliclorensin consists of a 3:1 mixture of the (S)- and (R)-enantiomers.