Stereoselective divergent synthesis of four diastereomers of pachastrissamine (jaspine B).
A divergent short synthesis of four diastereomers of pachastrissamine was achieved. Natural pachastrissamine was synthesized through bis-tosylation of the common intermediate and cyclization. 2-epi-Pachastrissamine was obtained by monotosylation and spontaneous cyclization of D-ribo-phytosphingosine derivative. By use of regio- and stereospecific ring-opening reaction of the orthoester assisted by a Boc group as a key step, 3-epi- and 2,3-epi-pachastrissamines were synthesized. The three stereogenic centers of all the diastereomers were constructed by using Garner's aldehyde as the sole chiral source.
Yoshimitsu
Yuji
Y
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
Inuki
Shinsuke
S
Oishi
Shinya
S
Fujii
Nobutaka
N
Ohno
Hiroaki
H
D000447:Aldehydes / Q000737:chemistry; D003500:Cyclization; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry
D000447:Aldehydes; D014105:Tosyl Compounds; C468594:pachastrissamine; D013110:Sphingosine