title: Total synthesis of aplyronine C.
abstract: A highly stereocontrolled total synthesis of the cytotoxic marine macrolide aplyronine C is described. The route exploits aldol methodology to install the requisite stereochemistry and features a crucial boron-mediated aldol coupling of an N-vinylformamide-bearing methyl ketone with a macrocyclic aldehyde to introduce the full side chain. The synthesis of two novel C21-C34 side chain analogs is also reported.
authors.affiliation: University Chemical Laboratory, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.
authors.forename: Ian
authors.initials: I
authors.lastname: Paterson
authors.forename: Sarah J
authors.initials: SJ
authors.lastname: Fink
authors.forename: Lydia Y W
authors.initials: LY
authors.lastname: Lee
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Atkinson
authors.forename: Simon B
authors.initials: SB
authors.lastname: Blakey
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001895:Boron / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D018942:Macrolides; D014753:Vinyl Compounds; C000588624:aplyronine C; D001895:Boron