title: Absolute stereochemistry of neohalicholactone from the brown alga Laminaria sinclairii.
abstract: Phytochemical analysis of an extract from the brown alga Laminaria sinclairii led to the isolation of neohalicholactone, a cyclopropyl-containing oxylipin previously isolated from a marine sponge, Halichondria okadai. Unequivocal stereochemical analysis of the C-15 hydroxyl group showed this isolate to be of opposite overall absolute stereochemistry compared to that proposed for halicholactone, a related compound from the sponge, and by our inference, sponge-derived neohalicholactone. Comparison of chiroptical data for all three compounds indicates the absolute stereochemistry of the sponge compounds is most probably opposite to that previously proposed.
authors.affiliation: College of Pharmacy, Oregon State University, Corvallis 97331.
authors.forename: P J
authors.initials: PJ
authors.lastname: Proteau
authors.forename: J V
authors.initials: JV
authors.lastname: Rossi
authors.forename: W H
authors.initials: WH
authors.lastname: Gerwick
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000459:Phaeophyceae / Q000737:chemistry*
chemical_list: D003521:Cyclopropanes; D007783:Lactones; C093031:neohalicholactone