Total synthesis of halipeptins: isolation of halipeptin D and synthesis of oxazoline halipeptin analogues.
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.
Nicolaou
K C
KC
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA.
Schlawe
Daniel
D
Kim
David W
DW
Longbottom
Deborah A
DA
de Noronha
Rita G
RG
Lizos
Dimitrios E
DE
Manam
Rama Rao
RR
Faulkner
D John
DJ
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
D047630:Depsipeptides; D010080:Oxazoles; C513526:halipeptin D