title: Total Synthesis of Solandelactone I.
abstract: Since the marine natural products solandelactones A-I were isolated from the hydroid Solanderia secunda and investigated by Seo et al. in 1996, considerable synthetic efforts toward these marine oxylipins followed. However, the structure elucidation of solandelactone I remained incomplete, and no synthesis has been reported. On the basis of our retrosynthetic analysis, the key building blocks were combined in a Horner-Wadsworth-Emmons reaction to create two common intermediates for the stereodivergent synthesis of all four diastereomers 1-4 matching the proposed structure of solandelactone I. Comparison of the published analytical data of natural product solandelactone I and data obtained from the synthetic endeavor toward diastereomers 1-4 enabled the structure assignment of isomer 3; the proposed biosynthetic pathway for marine oxylipins also supports the result.
authors.affiliation: Institut für Bioorganische Chemie, Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich , 52426 Jülich, Germany.
authors.forename: Nils C
authors.initials: NC
authors.lastname: Eichenauer
authors.affiliation: Institut für Bioorganische Chemie, Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich , 52426 Jülich, Germany.
authors.forename: Roxanne
authors.initials: R
authors.lastname: Tschersich
authors.affiliation: Institut für Bioorganische Chemie, Heinrich-Heine-Universität Düsseldorf im Forschungszentrum Jülich , 52426 Jülich, Germany.|Institut für Bio- und Geowissenschaften (IBG-1: Biotechnologie), Forschungszentrum Jülich , 52428 Jülich, Germany.
authors.forename: Jörg
authors.initials: J
authors.lastname: Pietruszka
mesh_terms: D001688:Biological Products / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D054883:Oxylipins / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D007783:Lactones; D054883:Oxylipins; C000605881:solandelactone I