title: (+)- and (-)-mutisianthol: first total synthesis, absolute configuration, and antitumor activity.
abstract: The first synthesis of the natural product (+)-mutisianthol was accomplished in 11 steps and in 21% overall yield from 2-methylanisole. The synthesis of its enantiomer was also performed in a similar overall yield. The absolute configuration of the sesquiterpene (+)-mutisianthol was assigned as (1S,3R). Key steps in the route are the asymmetric hydrogenation of a nonfunctionalized olefin using chiral iridium catalysts and the ring contraction of 1,2-dihydronaphthalenes using thallium(III) or iodine(III). The target molecules show moderate activity against the human tumor cell lines SF-295, HCT-8, and MDA-MB-435.
authors.affiliation: Department of Chemistry, Institute of Chemistry, University of Sao Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, CEP 05513-970 Sao Paulo SP, Brazil.
authors.forename: Graziela G
authors.initials: GG
authors.lastname: Bianco
authors.forename: Helena M C
authors.initials: HM
authors.lastname: Ferraz
authors.forename: Arinice M
authors.initials: AM
authors.lastname: Costa
authors.forename: Letícia V
authors.initials: LV
authors.lastname: Costa-Lotufo
authors.forename: Cláudia
authors.initials: C
authors.lastname: Pessoa
authors.forename: Manoel O
authors.initials: MO
authors.lastname: de Moraes
authors.forename: Marcus G
authors.initials: MG
authors.lastname: Schrems
authors.forename: Andreas
authors.initials: A
authors.lastname: Pfaltz
authors.forename: Luiz F
authors.initials: LF
authors.lastname: Silva
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000840:Anisoles / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006865:Hydrogenation; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000840:Anisoles; D000970:Antineoplastic Agents; D001688:Biological Products; D012717:Sesquiterpenes; C540246:mutisianthol; C428434:2-methylanisole