title: Synthesis and structural characterization of natural benzofuranoids.
abstract: The synthesis of ustusoranes A, B, and E, pergillin, dihydropergillin, (±)-penicisochroman A, and (-)-brassicadiol, starting from optically active (R)-benzolactone, is described. The synthesis of ustusoranes A and E established the absolute configurations of these natural products. The synthesis of pergillin and (±)-penicisochroman A led to the structural revision of aspergiones E and F. This study clearly indicates that (R)-benzolactone is a potential intermediate in the synthesis of natural benzofuranoids.
authors.affiliation: Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Sakyo-ku, Kyoto 606-8522, Japan.
authors.forename: Kouji
authors.initials: K
authors.lastname: Kuramochi
authors.affiliation: Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Sakyo-ku, Kyoto 606-8522, Japan.
authors.forename: Kazunori
authors.initials: K
authors.lastname: Tsubaki
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D001688:Biological Products; C000599819:ustusorane A; C000599820:ustusorane B; C000599821:ustusorane E