title: Stereoselective synthesis of L-threo-sphingosine, L-threo-sphinganine, D-threo-sphingosine, and D-threo-sphinganine via oxazoline formation and olefin cross-metathesis; potent protein kinase C inhibitor analogues.
abstract: In this study, we explored a convenient and concise route for synthesis of L-threo-sphingosine, D-threo-sphingosine, L-threo-sphinganine and D-threo-sphinganine from commercially available L- or D-serine. The key steps are the simple preparation of trans-oxazoline and intermolecular olefin cross metathesis.
authors: College of Pharmacy, SungKyunKwan University, Suwon 440-746, Korea.
authors: Yong-Shou
authors: YS
authors: Tian
authors: Jae-Eun
authors: JE
authors: Joo
authors: Van-Thoai
authors: VT
authors: Pham
authors: Kee-Young
authors: KY
authors: Lee
authors: Won-Hun
authors: WH
authors: Ham
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000475:Alkenes; D010080:Oxazoles; D047428:Protein Kinase Inhibitors; D011493:Protein Kinase C; D013110:Sphingosine; C005682:safingol