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.
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.
Tian
Yong-Shou
YS
College of Pharmacy, SungKyunKwan University, Suwon 440-746, Korea.
Joo
Jae-Eun
JE
Pham
Van-Thoai
VT
Lee
Kee-Young
KY
Ham
Won-Hun
WH
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
D000475:Alkenes; D010080:Oxazoles; D047428:Protein Kinase Inhibitors; D011493:Protein Kinase C; D013110:Sphingosine; C005682:safingol