title: Bioinspired total synthesis of (±)-yezo'otogirin C.
abstract: The first and protective group-free total synthesis of (±)-yezo'otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (±)-yezo'otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.
authors.affiliation: Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen University Town, Xili, Shenzhen 518055, China.
authors.forename: Shuzhong
authors.initials: S
authors.lastname: He
authors.forename: Wei
authors.initials: W
authors.lastname: Yang
authors.forename: Lizhi
authors.initials: L
authors.lastname: Zhu
authors.forename: Guangyan
authors.initials: G
authors.lastname: Du
authors.forename: Chi-Sing
authors.initials: CS
authors.lastname: Lee
mesh_terms: D002384:Catalysis; D003500:Cyclization; D003512:Cyclohexanones / Q000737:chemistry*; D020902:Hypericum / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry
chemical_list: D003512:Cyclohexanones; D013729:Terpenes; C000589995:yezo'otogirin C; D013890:Thiourea