title: Remarkable switch of regioselectivity in Diels-Alder reaction: divergent total synthesis of borreverine, caulindoles, and flinderoles.
abstract: Switchable reaction patterns of dimerization of indole substituted butadienes via a Lewis acid and thermal activation are reported. While under acidic conditions dimerization occurred around the internal double bond of the dienophile, a complete switch of regioselectivity was observed under thermal conditions, where dimerization occurred around the terminal double bond of the dienophile. This switch of regioselectivity was further exploited for the divergent total synthesis of structurally diverse indole alkaloid natural products.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Kanpur , Kanpur 208016, India.
authors.forename: Dattatraya H
authors.initials: DH
authors.lastname: Dethe
authors.forename: Rohan D
authors.initials: RD
authors.lastname: Erande
authors.forename: Balu D
authors.initials: BD
authors.lastname: Dherange
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002070:Butadienes / Q000737:chemistry; D061565:Cycloaddition Reaction; D019281:Dimerization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001688:Biological Products; D002070:Butadienes; D026121:Indole Alkaloids; D007211:Indoles; C538846:flinderole A; C538847:flinderole B; C538848:flinderole C; C027496:borreverine