title: Stereoselective synthesis of C18-guggultetrol and C18-phytosphingosine analogues from D-fructose.
abstract: A series of C(18)-guggultetrol stereo isomers and C(18)-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.
authors.affiliation: School of Chemistry, University of Hyderabad, Hyderabad, India. prssc@uohyd.ernet.in
authors.forename: Perali
authors.initials: P
authors.lastname: Ramu Sridhar
authors.forename: Mandava
authors.initials: M
authors.lastname: Suresh
authors.forename: Patteti
authors.initials: P
authors.lastname: Venu Kumar
authors.forename: Kalapati
authors.initials: K
authors.lastname: Seshadri
authors.forename: Chunduri
authors.initials: C
authors.lastname: Venkata Rao
mesh_terms: D001094:Arachidonate 5-Lipoxygenase / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005632:Fructose / Q000737:chemistry*; D015394:Molecular Structure; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D005233:Fatty Alcohols; D005632:Fructose; D001094:Arachidonate 5-Lipoxygenase; C012491:phytosphingosine; D013110:Sphingosine