Sariya YodwareeDarunee SoorukramChutima KuhakarnPatoomratana TuchindaVichai ReutrakulManat PohmakotrMahidol University2018-11-092018-11-092014-09-21Organic and Biomolecular Chemistry. Vol.12, No.35 (2014), 6885-6894147705202-s2.0-84906248897https://repository.li.mahidol.ac.th/handle/20.500.14594/33224The formal synthesis of (+)-3-epi-eupomatilone-6 (1) and the 3,5-bis-epimer (2) has been accomplished. The key synthetic strategy involved the stereoselective construction of (3R,4S,5R)- and (3R,4S,5S)-trisubstituted γ-butyrolactones 3 and 4 from (2R,3R)-2,3-dimethyl-4-pentenoic acid derivative 7, 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. This journal is © the Partner Organisations 2014.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryArticleSCOPUS10.1039/c4ob01078g