title: Total synthesis and absolute configuration of malyngamide W.
abstract: A concise enantioselective synthesis of malyngamide W (1) and its 2'-epimer was described. The strategy was based on three key steps: (1) ozonolysis of compound 11 which was derived from (R)-(-)-carvone 8, followed by copper-iron-catalyzed rearrangement to give the key cyclohex-2-enone intermediate 5, (2) Nozaki-Hiyama-Kishi coupling reaction between aldehyde 4 and iodide 14 to afford alcohol 3, and (3) asymmetric (R)-CBS reduction of the ketone functionality in compound 21 to establish the C-2' chiral center in the target compound 1. The absolute configuration of malyngamide W (1) was thus confirmed via the synthesis of 1 and 2'-epi-1.
authors: State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P R China.
authors: Xian-Liang
authors: XL
authors: Qi
authors: Jun-Tao
authors: JT
authors: Zhang
authors: Jian-Peng
authors: JP
authors: Feng
authors: Xiao-Ping
authors: XP
authors: Cao
mesh_terms: D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry*; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D003512:Cyclohexanones; D005229:Fatty Acids, Monounsaturated; C474705:malyngamide W