title: Synthesis of a natural chromenoquinone via the Diels-Alder reaction of pyranobenzyne and furan.
abstract: We describe the total synthesis of angular chromenoquinone 1 isolated from Conospermum plants. Iodophenol, a precursor of pyranobenzyne, was prepared by Claisen rearrangement of an iodoresorcinol derivative. Diels-Alder reaction of the pyranobenzyne and a substituted furan proceeded in low regioselectivity to afford desired 1 and its regioisomer.
authors.affiliation: Department of Synthetic Organic Chemistry, Research Institute of Pharmaceutical Sciences, Musashino University.
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Katakawa
authors.forename: Ayaka
authors.initials: A
authors.lastname: Sato
authors.forename: Mari
authors.initials: M
authors.lastname: Iwasaki
authors.forename: Tomofumi
authors.initials: T
authors.lastname: Horikawa
authors.forename: Takuya
authors.initials: T
authors.lastname: Kumamoto
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D005663:Furans; D039105:Proteaceae / Q000737:chemistry*; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D001688:Biological Products; D005663:Furans; D011809:Quinones; C039281:furan