title: Total synthesis of thaxtomin A and its stereoisomers and findings of their biological activities.
abstract: The first and facile total synthesis of thaxtomin A and its three stereoisomers has been achieved. The synthetic approach involves intramolecular nucleophilic cyclization of an amide toward a ketoamide group to produce a C-hydroxydiketopiperazine scaffold. The most amazing discovery was that each of the four stereoisomers of TA exhibits different phytotoxic, fungicidal, and antiviral activities.
authors.affiliation: State Key Laboratory of Elemento-organic Chemistry, College of Pharmacy, and College of Chemistry, Nankai University , Tianjin 300071, PR China.
authors.forename: Hongbo
authors.initials: H
authors.lastname: Zhang
authors.forename: Xin
authors.initials: X
authors.lastname: Ning
authors.forename: Hang
authors.initials: H
authors.lastname: Hang
authors.forename: Xuyan
authors.initials: X
authors.lastname: Ru
authors.forename: Haichen
authors.initials: H
authors.lastname: Li
authors.forename: Yonghong
authors.initials: Y
authors.lastname: Li
authors.forename: Lizhong
authors.initials: L
authors.lastname: Wang
authors.forename: Xiao
authors.initials: X
authors.lastname: Zhang
authors.forename: Shujing
authors.initials: S
authors.lastname: Yu
authors.forename: Yuanyuan
authors.initials: Y
authors.lastname: Qiao
authors.forename: Xin
authors.initials: X
authors.lastname: Wang
authors.forename: Peng George
authors.initials: PG
authors.lastname: Wang
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D000935:Antifungal Agents; D000998:Antiviral Agents; D007211:Indoles; D010879:Piperazines; C406691:thaxtomine A