title: Formal synthesis of (+)-3-epi-eupomatilone-6 and the 3,5-bis-epimer.
abstract: The formal synthesis of (+)-3-epi-eupomatilone-6 () and the 3,5-bis-epimer () has been accomplished. The key synthetic strategy involved the stereoselective construction of (3R,4S,5R)- and (3R,4S,5S)-trisubstituted γ-butyrolactones and from (2R,3R)-2,3-dimethyl-4-pentenoic acid derivative , which was readily obtained via stereoselective conjugate addition of vinylmagnesium chloride to a chiral α,β-unsaturated N-acyl oxazolidinone (Evans' auxiliary) followed by α-methylation.
authors: Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand. darunee.soo@mahidol.ac.th.
authors: Sariya
authors: S
authors: Yodwaree
authors: Darunee
authors: D
authors: Soorukram
authors: Chutima
authors: C
authors: Kuhakarn
authors: Patoomratana
authors: P
authors: Tuchinda
authors: Vichai
authors: V
authors: Reutrakul
authors: Manat
authors: M
authors: Pohmakotr
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D002712:Chlorides / Q000737:chemistry; D015195:Drug Design; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015636:Magnesium Chloride / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D002712:Chlorides; D006847:Hydrocarbons, Iodinated; D007783:Lactones; D010936:Plant Extracts; C485126:eupomatilone-6; D015636:Magnesium Chloride; C014055:methyl iodide