SYNTHESIS OF A DEOXYNOJIRIMYCIN ANALOG FROM CASTANOSPERMINE

Ring cleavage of 1,6-O, O-bis-t-butyldimethylsilylcastanospermine 3 wi th methyl chloroformate followed by deprotection with tetrabutylammoni um fluoride gave aR)-1-(2'-chloroetbyl)-1,5,6,7,8,8a-hexahydro-6,7, hy dro-6,7,8-trihydroxy-3H-furo[3,4-a]pyridin-3-one 5. Refluxing 5 with p otassium t-butoxide, followed by the addition of NaOH and futher reflu xing yielded the deoxynojirimycin analogue ,4R,5S)-2-(1'-hydroxy-2'-pr openyl)-piperidine-3,4, 5-triol 2. Copyright (C) 1996 Elsevier Science Ltd