title: Total synthesis of C19 lipid diols containing a 2,5-disubstituted-3-oxygenated tetrahydrofuran.
abstract: The total synthesis of the C(19) lipid diols 5 and 6, the enantiomers of the anthelmintic marine natural products 1 and 3, is described. Key steps in the divergent syntheses include a syn selective epoxidation of a homoallylic alcohol, a one-pot alkoxypalladation-carbonylation-lactonisation reaction sequence and a DMEAD promoted Mitsunobu inversion.
authors.affiliation: School of Chemistry, The University of Sydney, NSW, 2006, Australia.
authors.forename: Caroline L
authors.initials: CL
authors.lastname: Nesbitt
authors.forename: Christopher S P
authors.initials: CS
authors.lastname: McErlean
mesh_terms: D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D008055:Lipids / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*
chemical_list: D005663:Furans; D008055:Lipids; C018674:tetrahydrofuran; D010100:Oxygen