title: Total synthesis of halipeptins: isolation of halipeptin D and synthesis of oxazoline halipeptin analogues.
abstract: The isolation from the marine sponge Leiosella cf. arenifibrosa and structural elucidation of halipeptin D (5), a relative of the previously isolated halipeptins A-C (1-3), is described along with the total synthesis of a number of oxazoline analogues (7 a-d and epi-7 c-d). The developed synthetic strategy provides a flexible entry into the various isomers of the polyketide domain of the halipeptins and improvises for a late stage construction of the oxazoline ring after a macrolactamization process which secures the required macrocycle.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA.
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: Daniel
authors.initials: D
authors.lastname: Schlawe
authors.forename: David W
authors.initials: DW
authors.lastname: Kim
authors.forename: Deborah A
authors.initials: DA
authors.lastname: Longbottom
authors.forename: Rita G
authors.initials: RG
authors.lastname: de Noronha
authors.forename: Dimitrios E
authors.initials: DE
authors.lastname: Lizos
authors.forename: Rama Rao
authors.initials: RR
authors.lastname: Manam
authors.forename: D John
authors.initials: DJ
authors.lastname: Faulkner
mesh_terms: D000818:Animals; D003500:Cyclization; D047630:Depsipeptides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010080:Oxazoles / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D047630:Depsipeptides; D010080:Oxazoles; C513526:halipeptin D