title: A one-pot multicomponent coupling/cyclization for natural product herbicide (±)-thaxtomin A.
abstract: Herbicide (±)-thaxtomin A has been synthesized in a one-pot process with a 32% isolated yield. A multicomponent coupling reaction was utilized to prepare in situ a dipeptide precursor which then sequentially underwent an alkaline mediated keto-amide cyclization to provide the target molecule. Adjustment of diastereoselectivity was achieved using microwave-induced irradiation. The approach incorporates atom economy and reaction efficiency and allows for facile library development.
authors: Department of Chemistry and Biochemistry, School of Green Chemistry and Engineering, University of Toledo, 2801 W. Bancroft St, Toledo, OH 43606, USA. peter.andreana@utoledo.edu.
authors: Jean Paul
authors: JP
authors: Bourgault
authors: Amarendar Reddy
authors: AR
authors: Maddirala
authors: Peter R
authors: PR
authors: Andreana
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D006540:Herbicides; D007211:Indoles; D010879:Piperazines; C406691:thaxtomine A