title: Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of beta-hydroxycarbonyl compounds.
abstract: A versatile approach for the enantioselective synthesis of functionalised beta-hydroxy N-acetylcysteamine thiol esters has been developed which allows the facile incorporation of isotopic labels. It has been shown that a remarkable reversal of selectivity occurs in the titanium mediated aldol reaction of acyloxazolidinone using either (S)- or (R)-tert-butyldimethylsilyloxybutanal. The aldol products are valuable intermediates in the synthesis of 4-hydroxy-6-substituted delta-lactones.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol, UKBS8 1TS.
authors.forename: Christine
authors.initials: C
authors.lastname: Le Sann
authors.forename: Dulce M
authors.initials: DM
authors.lastname: Munoz
authors.forename: Natalie
authors.initials: N
authors.lastname: Saunders
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Simpson
authors.forename: David I
authors.initials: DI
authors.lastname: Smith
authors.forename: Florilène
authors.initials: F
authors.lastname: Soulas
authors.forename: Paul
authors.initials: P
authors.lastname: Watts
authors.forename: Christine L
authors.initials: CL
authors.lastname: Willis
mesh_terms: D007659:Ketones / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D018942:Macrolides