title: A novel and efficient synthesis of diverse dihydronaphtho[1,2-b]furans using the ceric ammonium nitrate-catalyzed formal [3 + 2] cycloaddition of 1,4-naphthoquinones to olefins and its application to furomollugin.
abstract: A novel approach was developed for the synthesis of diverse dihydronaphtho[1,2-b]furans from 1,4-naphthoquinones and olefins in the presence of ceric ammonium nitrate. This reaction provides a rapid route for the synthesis of a variety of dihydronaphtho[1,2-b]furans and naphtho[1,2-b]furans bearing different substituents. This methodology was also used to synthesize the biologically important natural product furomollugin in only 2 steps.
authors: School of Chemical Engineering, Yeungnam University, Gyeongsan 712-749, Republic of Korea.
authors: Likai
authors: L
authors: Xia
authors: Yong Rok
authors: YR
authors: Lee
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D002563:Cerium / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D009285:Naphthoquinones / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D001688:Biological Products; D005663:Furans; D006575:Heterocyclic Compounds, 3-Ring; D009284:Naphthols; D009285:Naphthoquinones; D011753:Pyrones; C102708:furomollugin; D002563:Cerium; C035342:1,4-naphthoquinone; C004653:ceric ammonium nitrate