title: Noteworthy observations accompanying synthesis of the apoptolidin disaccharide.
abstract: A stereoselective synthesis of the apoptolidin disaccharide is reported. The key chemistry features a new transformation utilizing a highly selective tetramethylalkoxyalanate[v]-directed syn-methylation of a vinylogous ester, isolation of a hydrate of a 2-keto sugar, an eco-friendly radical cleavage of a bromomethyl group, and an efficient preparation of a fluorodisaccharide via the use of XtalFluor-E.
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
authors.forename: Madduri
authors.initials: M
authors.lastname: Srinivasarao
authors.forename: Taesik
authors.initials: T
authors.lastname: Park
authors.forename: Yuzhong
authors.initials: Y
authors.lastname: Chen
authors.forename: Philip L
authors.initials: PL
authors.lastname: Fuchs
mesh_terms: D004187:Disaccharides / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004187:Disaccharides; D018942:Macrolides; D011753:Pyrones; C506738:apoptolidin A; C518447:apoptolidin D; C114125:apoptolidin