title: Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core.
abstract: We report herein a facile and efficient method of the construction of the cis-1,2-oxazadecaline system, distinctive of (pre)trichodermamides, aspergillazine A, gliovirin, and FA-2097. The formation of the 1,2-oxazadecaline core was accomplished by a 1,2-addition of an αC-lithiated O-silyl ethyl pyruvate oxime to benzoquinone, which is followed by an oxa-Michael ring-closure. The method was successfully applied to the concise total synthesis of trichodermamide A (in gram quantities) and trichodermamide B, as well as the first synthesis of trichodermamide C.
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States.
authors.forename: Adelphe M
authors.initials: AM
authors.lastname: Mfuh
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States.
authors.forename: David E
authors.initials: DE
authors.lastname: Stephens
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States.
authors.forename: Anh X T
authors.initials: AX
authors.lastname: Vo
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States.
authors.forename: Hadi D
authors.initials: HD
authors.lastname: Arman
authors.affiliation: Department of Chemistry, University of Texas at San Antonio, San Antonio, Texas 78249, United States.
authors.forename: Oleg V
authors.initials: OV
authors.lastname: Larionov
mesh_terms: D016227:Benzoquinones / Q000138:chemical synthesis / Q000737:chemistry; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D016227:Benzoquinones; D004151:Dipeptides; D004224:Diterpenes; D010091:Oximes; C476747:trichodermamide A; C476748:trichodermamide B; C529906:trichodermamide C; C004532:quinone