title: Total synthesis of (+)-trans-trikentrin A.
abstract: Several syntheses have already been reported for cis-trikentrins and herbindoles, which are indole alkaloids unsubstituted at the C2 and C3 positions that bear a trans-1,3-dimethylcyclopentyl unit. Herein, we describe the first asymmetric and stereoselective synthesis of the more challenging trans-trikentrin A as its naturally occurring isomer. Different approaches were investigated and the strategy of choice was a combination of an enzymatic kinetic resolution and a thallium(III)-mediated ring contraction. The antiproliferative activities of the natural product and related intermediates have been tested against human tumor cell lines, leading to the discovery of new compounds with potent antitumor activity.
authors.affiliation: Instituto de Química, Universidade de São Paulo, Brazil.
authors.forename: Iris R M
authors.initials: IR
authors.lastname: Tébéka
authors.forename: Giovanna B
authors.initials: GB
authors.lastname: Longato
authors.forename: Marcus V
authors.initials: MV
authors.lastname: Craveiro
authors.forename: João E
authors.initials: JE
authors.lastname: de Carvalho
authors.forename: Ana L T G
authors.initials: AL
authors.lastname: Ruiz
authors.forename: Luiz F
authors.initials: LF
authors.lastname: Silva
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002522:Chlorocebus aethiops; D055808:Drug Discovery; D019008:Drug Resistance, Neoplasm; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D014709:Vero Cells
chemical_list: D000970:Antineoplastic Agents; D026121:Indole Alkaloids; C519345:trikentrin A