title: An efficient synthesis of the natural tetrahydrofuran pachastrissamine starting from D-ribo-phytosphingosine.
abstract: [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.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Richard J B H N
authors.initials: RJ
authors.lastname: van den Berg
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Boltje
authors.forename: Carlo P
authors.initials: CP
authors.lastname: Verhagen
authors.forename: Remy E J N
authors.initials: RE
authors.lastname: Litjens
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
mesh_terms: 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
chemical_list: D005663:Furans; D007202:Indicators and Reagents; C468594:pachastrissamine; C018674:tetrahydrofuran; D012266:Ribose; C012491:phytosphingosine; D013110:Sphingosine