Stereoselective synthesis of C18-guggultetrol and C18-phytosphingosine analogues from D-fructose

Perali Ramu Sridhar; Mandava Suresh; Patteti Venu Kumar; Kalapati Seshadri; Chunduri Venkata Rao

doi:10.1016/j.carres.2012.07.016

Stereoselective synthesis of C18-guggultetrol and C18-phytosphingosine analogues from D-fructose

Carbohydr Res. 2012 Oct 1:360:40-6. doi: 10.1016/j.carres.2012.07.016. Epub 2012 Aug 4.

Authors

Perali Ramu Sridhar¹, Mandava Suresh, Patteti Venu Kumar, Kalapati Seshadri, Chunduri Venkata Rao

Affiliation

¹ School of Chemistry, University of Hyderabad, Hyderabad, India. prssc@uohyd.ernet.in

PMID: 22975277
DOI: 10.1016/j.carres.2012.07.016

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Arachidonate 5-Lipoxygenase / metabolism*
Dose-Response Relationship, Drug
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / pharmacology
Fatty Alcohols / chemical synthesis*
Fatty Alcohols / chemistry
Fatty Alcohols / pharmacology*
Fructose / chemistry*
Molecular Structure
Sphingosine / analogs & derivatives*
Sphingosine / chemical synthesis
Sphingosine / chemistry
Sphingosine / pharmacology
Stereoisomerism
Structure-Activity Relationship

Substances

Enzyme Inhibitors
Fatty Alcohols
Fructose
Arachidonate 5-Lipoxygenase
phytosphingosine
Sphingosine