title: Synthesis of a pladienolide B analogue with the fully functionalized core structure.
abstract: Starting from (R)-(-)-linalool (6), terminus differentiation and chain extension via aldol type reactions led to ketophosphonate 16 (C1-C8 building block). In a Horner-Wadsworth-Emmons reaction, 16 reacted with aldehyde 22, which contained the vicinal anti-Me-OH pattern and a vinyl iodide function, to provide the C1-C13 part of pladienolide B. After Shiina macrolactonization, reduction of the enone 26 gave the core structure 27. A Stille cross-coupling of vinyl iodide 27 with tributylphenylstannane eventually furnished analogue 30.
authors.affiliation: Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany.
authors.forename: Sarah
authors.initials: S
authors.lastname: Müller
authors.forename: Timo
authors.initials: T
authors.lastname: Mayer
authors.forename: Florenz
authors.initials: F
authors.lastname: Sasse
authors.forename: Martin E
authors.initials: ME
authors.lastname: Maier
mesh_terms: D004852:Epoxy Compounds / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D004852:Epoxy Compounds; D018942:Macrolides; C522342:pladienolide B