2-Hydroxycastanospermines (dihydroxy-L-swainsonines) from octonolactones: Inhibition of naringinase (L-rhamnosidase)

Article abstract of DOI:10.1016/0040-4039(96)01956-9

Short syntheses of 2S-2-hydroxycastanospermine, and 2R- and 2S-2-hydroxy-6-epicastanospermine - in which there are 6 adjacent chiral centres and 8 contiguous carbon atoms containing functional groups from eight carbon sugar lactones - depend on efficient cyclisations to give piperidines with trans-acetonides as protecting groups. Inhibition of naringinase (L-rhamnosidase) by 2S-2-hydroxy-6-epicastanospermine and 2S-2-hydroxycastanospermine may be due to a structural resemblance to the unnatural L-(+)-swainsonine.