title: First synthesis of (+)-myrrhanol C, an anti-prostate cancer lead.
abstract: The first synthesis of (+)-myrrhanol C (1), an antitumor polypodane-type bicyclic triterpene with inhibitory activity against androgen insensitive prostate cancers, is reported herein (IC(50) 10 μmolar). A key step in our convergent synthesis of (+)-myrrhanol C and related analogues is the employment of a microbial stereo- and regioselective late stage C-H oxidation. A low-waste and sustainable process has been developed to prepare (+)-myrrhanol C for further biological studies.
authors.affiliation: Department of Organic Chemistry, Institute of Biotechnology, Faculty of Sciences, University of Granada, Campus de Fuente Nueva, s/n, 18071 Granada, Spain. vdomingo@ugr.es
authors.forename: Victoriano
authors.initials: V
authors.lastname: Domingo
authors.forename: Lidia
authors.initials: L
authors.lastname: Lorenzo
authors.forename: José F
authors.initials: JF
authors.lastname: Quilez del Moral
authors.forename: Alejandro F
authors.initials: AF
authors.lastname: Barrero
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000627:therapeutic use; D060326:Chemistry Techniques, Synthetic; D015195:Drug Design; D006801:Humans; D007700:Kinetics; D008297:Male; D011471:Prostatic Neoplasms / Q000188:drug therapy*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000627:therapeutic use
chemical_list: D000970:Antineoplastic Agents; D014315:Triterpenes; C581429:myrrhanol C