title: Stereocontrolled synthesis of the C8-C22 fragment of rhizopodin.
abstract: A convergent synthesis of the central C8-C22 core of the potent macrolide antibiotic rhizopodin is reported. Notable features of the stereocontrolled approach include an asymmetric reverse prenylation of an alcohol using a method of Krische, a thiazolium catalyzed transformation of an epoxyaldehyde as described by Bode, and a late-stage oxazole formation from advanced intermediates. This route demonstrates the applicability of these methodologies in complex natural product synthesis.
authors.affiliation: Universität Heidelberg, Institut für Organische Chemie, INF 270, D-69120 Heidelberg, Germany.
authors.forename: Manuel
authors.initials: M
authors.lastname: Kretschmer
authors.forename: Dirk
authors.initials: D
authors.lastname: Menche
mesh_terms: D002384:Catalysis; D018942:Macrolides; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; D010080:Oxazoles; C081739:rhizopodin