title: Biomimetic total syntheses of borreverine and flinderole alkaloids.
abstract: Dimeric indole alkaloids represent a structurally unique class of natural products having interesting biological activities. Recently, we reported the first total synthesis of flinderoles B and C, structurally unique and potent antimalarial natural products. Central to the design of the approach and by virtue of a one-pot, acid-catalyzed dimerization reaction, the route also provided total synthesis of the borreverine class of natural products. This full account details the progress of efforts that culminated in the protecting-group-free, six-step total synthesis of all of the flindersia alkaloids: dimethylisoborreverine, isoborreverine, flinderoles A-C, and their analogues. A biomimetic approach featuring a scalable and catalytic formal [3 + 2] cycloaddition and Diels-Alder reaction is outlined in detail. On the basis of the experimental observations, a detailed mechanism has been proposed for the dimerization of tertiary alcohol 28.
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: Alok
authors.initials: A
authors.lastname: Ranjan
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products; D032701:Biomimetics; D061565:Cycloaddition Reaction; D019281:Dimerization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000962:Antimalarials; D001688:Biological Products; D026121:Indole Alkaloids; D007211:Indoles; C538847:flinderole B; C538848:flinderole C; C027496:borreverine