An efficient synthesis of the natural tetrahydrofuran pachastrissamine starting from D-ribo-phytosphingosine.
[reaction: see text] The natural product pachastrissamine, an anhydrophytosphingosine derivative isolated from various sponges and endowed with cytotoxic activity against several human carcinoma cell lines, was synthesized in three steps and with 72% overall yield from d-ribo-phytosphingosine.
van den Berg
Richard J B H N
RJ
Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
Boltje
Thomas J
TJ
Verhagen
Carlo P
CP
Litjens
Remy E J N
RE
van der Marel
Gijsbert A
GA
Overkleeft
Herman S
HS
D005663:Furans / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D012266:Ribose; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D005663:Furans; D007202:Indicators and Reagents; C468594:pachastrissamine; C018674:tetrahydrofuran; D012266:Ribose; C012491:phytosphingosine; D013110:Sphingosine