title: An improved asymmetric synthesis of malyngamide U and its 2'-epimer.
abstract: An accelerated and improved asymmetric synthesis of malyngamide U (1) and its 2'-epimer (2'-epi-1) was accomplished from readily available n-hexanal, ethanolamine and (R)-(-)-carvone. The key steps involved a Johnson-Claisen rearrangement in the synthesis of an unsaturated carboxylic acid 4 and an aldol reaction in the construction of the skeleton of 1 and 2'-epi-1. There are 13 steps in the synthesis, with a 2.7% overall yield for 1 and a 0.4% yield for 2'-epi-1.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, PR China.
authors.forename: Jian-Peng
authors.initials: JP
authors.lastname: Feng
authors.forename: Zi-Fa
authors.initials: ZF
authors.lastname: Shi
authors.forename: Yang
authors.initials: Y
authors.lastname: Li
authors.forename: Jun-Tao
authors.initials: JT
authors.lastname: Zhang
authors.forename: Xian-Liang
authors.initials: XL
authors.lastname: Qi
authors.forename: Jie
authors.initials: J
authors.lastname: Chen
authors.forename: Xiao-Ping
authors.initials: XP
authors.lastname: Cao
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones / Q000138:chemical synthesis*; D019856:Ethanolamine / Q000737:chemistry*; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis*; D008956:Models, Chemical; D039821:Monoterpenes / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000447:Aldehydes; D002264:Carboxylic Acids; D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones; D005229:Fatty Acids, Monounsaturated; D039821:Monoterpenes; C474704:malyngamide U; D019856:Ethanolamine; C006923:carvone; C010463:n-hexanal