Stereoselective synthesis of C18-guggultetrol and C18-phytosphingosine analogues from d-fructose Original Research Article

A series of C18-guggultetrol stereo isomers and C18-phytosphingosine regio/stereo isomers were synthesised in a stereoselective fashion involving metal mediated fragmentation, stereoselective reduction, 1,4 O→O silyl migration, and Grubbs’ cross metathesis as key steps. d-Fructose was used as a raw material for the preparation of all the analogues. The isophytosphingosine derivatives were evaluated against their 5-LOX (5-lipoxigenase) inhibitory activity.