title: Stereochemical diversity through cyclodimerization: synthesis of polyketide-like macrodiolides.
abstract: [reaction: see text] An expeditious procedure for the direct formation of stereochemically well-defined macrodiolides is described. Cyclodimerizations of enantioenriched C7 and C8 hydroxy esters 6 in the presence of catalytic amounts of distannoxane transesterification catalysts afford 14- to 22-membered macrodiolides 7-9 bearing up to six stereocenters. Additional structural diversity is introduced by further stereoselective reactions on selected macrodiolides 7a, 7g, 10a, and 11.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
authors.forename: Qibin
authors.initials: Q
authors.lastname: Su
authors.forename: Aaron B
authors.initials: AB
authors.lastname: Beeler
authors.forename: Emil
authors.initials: E
authors.lastname: Lobkovsky
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
authors.forename: James S
authors.initials: JS
authors.lastname: Panek
mesh_terms: D002384:Catalysis; D003500:Cyclization; D019281:Dimerization; D004951:Esterification; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D018942:Macrolides