title: Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation.
abstract: Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.
authors.affiliation: a Department of Pharmaceutical Sciences, Faculty of Pharmacy , Keio University , Tokyo , Japan.
authors.forename: Yasunobu
authors.initials: Y
authors.lastname: Yamashita
authors.affiliation: a Department of Pharmaceutical Sciences, Faculty of Pharmacy , Keio University , Tokyo , Japan.|b Department of Chemistry , Graduate School of SIGMA Clermont , Aubiere Cedex , France.
authors.forename: Alan
authors.initials: A
authors.lastname: Biard
authors.affiliation: a Department of Pharmaceutical Sciences, Faculty of Pharmacy , Keio University , Tokyo , Japan.
authors.forename: Kengo
authors.initials: K
authors.lastname: Hanaya
authors.affiliation: a Department of Pharmaceutical Sciences, Faculty of Pharmacy , Keio University , Tokyo , Japan.
authors.forename: Mitsuru
authors.initials: M
authors.lastname: Shoji
authors.affiliation: a Department of Pharmaceutical Sciences, Faculty of Pharmacy , Keio University , Tokyo , Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Sugai
mesh_terms: D000107:Acetylation; D060326:Chemistry Techniques, Synthetic / Q000191:economics / Q000379:methods*; D044950:Flavanones / Q000138:chemical synthesis*; D005419:Flavonoids / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D044950:Flavanones; D005419:Flavonoids; D005960:Glucosides; D013267:Stilbenes; C121481:astringin; C043561:chrysin; C085514:wogonin; C058229:polydatin
keywords: astringin; hydroxylation; site-selective acetylation; site-selective deacetylation; wogonin