A concise synthesis of a promising protein kinase C inhibitor: D-erythro-sphingosine.
In this study, we explored a convenient and concise route for synthesis of D-erythro-sphingosine 1 from commercially available and cheap L-serine. The key steps are simple preparation of amino ketone 5 from Weinreb amide 3 and high diastereoselective reduction of amino ketone 5 to give the natural erythro-(anti-) isomer.
Pham
Van-Thoai
VT
College of Pharmacy, SungKyunKwan University, Suwon 440-746, Korea.
Joo
Jae-Eun
JE
Tian
Yong-Shou
YS
Oh
Chang-Young
CY
Ham
Won-Hun
WH
D000577:Amides / Q000138:chemical synthesis; D002626:Chemistry, Pharmaceutical; D007659:Ketones / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*; D047428:Protein Kinase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D012694:Serine / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013237:Stereoisomerism; D013678:Technology, Pharmaceutical / Q000379:methods*
D000577:Amides; D007659:Ketones; D047428:Protein Kinase Inhibitors; C481931:erythro-(2R,3S)-sphingosine; D012694:Serine; D011493:Protein Kinase C; D013110:Sphingosine