Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine [jaspine B].
A practical stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B) was achieved in 48% overall yield from D-(-)-tartaric acid. Key features of the sequence include the diastereoselective formation of a tetrol with three contiguous chiral centers, which was further elaborated to pachastrissamine. The synthetic route is operationally simple, diastereoselective and is amenable for the synthesis of a number of analogues of pachastrissamine.
Prasad
Kavirayani R
KR
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, India. prasad@orgchem.iisc.ernet.in
Chandrakumar
Appayee
A
D002625:Chemistry, Organic / Q000379:methods*; D008956:Models, Chemical; D015394:Molecular Structure; D013107:Sphingolipids / Q000737:chemistry; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D013107:Sphingolipids; C468594:pachastrissamine; D013110:Sphingosine