title: Asymmetric total synthesis of fusarentin 6-methyl ether and its biomimetic transformation into fusarentin 6,7-dimethyl ether, 7-O-demethylmonocerin, and (+)-monocerin.
abstract: A concise asymmetric total synthesis of a fusarentin ether (1) with sequential biomimetic transformation to its analogues fusarentin 6,7-dimethyl ether (2), 7-O-demethylmonocerin (3), and (+)-monocerin (4) has been accomplished. The cis-fused furobenzopyranones of 7-O-demethylmonocerin (3) and (+)-monocerin (4) were efficiently constructed via an intramolecular nucleophilic trapping of a quinonemethide intermediate, which was obtained by benzylic oxidation of fusarentin 6-methyl ether (1) using hypervalent iodine reagent.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, People's Republic of China.
authors.forename: Bowen
authors.initials: B
authors.lastname: Fang
authors.forename: Xingang
authors.initials: X
authors.lastname: Xie
authors.forename: Changgui
authors.initials: C
authors.lastname: Zhao
authors.forename: Peng
authors.initials: P
authors.lastname: Jing
authors.forename: Huilin
authors.initials: H
authors.lastname: Li
authors.forename: Zhengshen
authors.initials: Z
authors.lastname: Wang
authors.forename: Jixiang
authors.initials: J
authors.lastname: Gu
authors.forename: Xuegong
authors.initials: X
authors.lastname: She
mesh_terms: D001578:Benzopyrans / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D005670:Fusarium / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D008738:Methyl Ethers / Q000138:chemical synthesis*; D018716:Molecular Mimicry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D001578:Benzopyrans; D005663:Furans; D007783:Lactones; D008738:Methyl Ethers; C493951:furobenzopyranone; C485193:monocerin