Functionalization of olefins by pendant sulfoxide: Toward stereoselective synthesis of D-ribo-(2S,3S,4R)-phytosphingosine

ORGN 711

Abdul Rasheed Mohammed, rasheed@suven.com1, Ramakrishna Nirogi1, and Raghavan Sadagopan, purush101@yahoo.com2. (1) Medicinal chemistry, Suven Life Sciences Limited, Serene chambers, Road-5, Avenue-7, Banjara Hills, Hyderabad-500034, India, (2) Organic Chemistry, Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India
A great deal of effort has been devoted towards the synthesis of Phytosphingosine, a backbone base of sphingolipids as it possesses a broad range of biological activities including anitmicrobial and anti-inflammatory properties. Recent studies also show phytosphingosine inducing apoptotic cell death in human cancer cells. Intra molecular sulfoxide group has been used as internal nucleophile in stereo-selective functionalization of olefins to form bromohydrin, which in turn, on functional transformation lead to the key intermediate. The key intermediate could be transformed to D-ribo-Phytosphingosine in a single hydrogenation step.