title: Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone E.
abstract: A protecting-group-free total synthesis of (+)-goniodiol (1), (6S,7S,8S)-goniodiol (2), (-)-parvistone D (4), and (+)-parvistone E (6) was efficiently achieved in five steps from commercially available trans-cinnamaldehyde with high overall yields (72-75%). The synthesis strategy was inspired from the proposed biosynthesis pathway of styryllactones. Key transformations of the strategy include a one-pot conversion of goniothalamin oxide to goniodiol or 9-deoxygoniopypyrone in aqueous media, stereoselective epoxidation, ring-closing metathesis, and stereoselective Maruoka allylation. The route is amenable to synthesis of various analogues for biological evaluation.
authors: Division of Natural Products Chemistry and ‡Centre for NMR and Structural Chemistry, Indian Institute of Chemical Technology , Tarnaka, Hyderabad-500007, India.
authors: Perla
authors: P
authors: Ramesh
authors: Division of Natural Products Chemistry and ‡Centre for NMR and Structural Chemistry, Indian Institute of Chemical Technology , Tarnaka, Hyderabad-500007, India.
authors: Tadikamalla P
authors: TP
authors: Rao
mesh_terms: D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000378:metabolism; D008968:Molecular Conformation; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D011753:Pyrones; C446739:goniodiol; C000617731:parvistone D; C073078:9-deoxygoniopypyrone; C103280:goniothalamin