title: First total synthesis of tubulysin B.
abstract: The first total synthesis of tubulysin B is described. The aziridine route to tubuphenylalanine (Tup) of the tubulysin D/U-series could not be transferred to the synthesis of tubutyrosine (blue moiety). Therefore, tubutyrosine (Tut) was synthesized by a Wittig olefination/diastereoselective catalytic reduction sequence. Interestingly, the C-2 epimer of tubulysin B has a cytotoxic activity almost identical to the natural diastereomer.
authors.affiliation: Leibniz Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, D-06120 Halle (Saale), Germany.
authors.forename: Orlando
authors.initials: O
authors.lastname: Pando
authors.forename: Simon
authors.initials: S
authors.lastname: Dörner
authors.forename: Rainer
authors.initials: R
authors.lastname: Preusentanz
authors.forename: Annika
authors.initials: A
authors.lastname: Denkert
authors.forename: Andrea
authors.initials: A
authors.lastname: Porzel
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Richter
authors.forename: Ludger
authors.initials: L
authors.lastname: Wessjohann
mesh_terms: D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D050257:Tubulin Modulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D009842:Oligopeptides; D010875:Pipecolic Acids; D050257:Tubulin Modulators; C546650:tubulysin B