%0 Journal Article %A Chin, Yen-Jin %A Wang, Shun-Yi %A Loh, Teck-Peng %D 2009 %T Synthesis of Iriomoteolide-1a C13−C23 Fragment via Asymmetric Conjugate Addition and Julia−Kocienski Coupling Reaction %U https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Iriomoteolide_1a_C13_C23_Fragment_via_Asymmetric_Conjugate_Addition_and_Julia_Kocienski_Coupling_Reaction/2834320 %R 10.1021/ol901480s.s001 %2 https://acs.figshare.com/ndownloader/files/4532017 %K methylmagnesium bromide %K 6. %K olefination %K aldehyde 5 %K Fragment %K ester %K Asymmetric Conjugate Addition %K stereoselective introduction %K acetonide %K synthesis %K Iriomoteolide %K fragment %K conjugate addition %K iriomoteolide %K Julia %K Synthesi %K C 29 methyl group %X The key C13−C23 fragment toward the total synthesis of iriomoteolide-1a (1) has been constructed from an 1,2-acetonide containing aldehyde 5 via a Julia−Kocienski olefination with the C16−C23 segment 6. The key step involves stereoselective introduction of the C29 methyl group by a highly efficient CuI-Tol-BINAP-catalyzed asymmetric conjugate addition of methylmagnesium bromide to an α,β-unsaturated ester. %I ACS Publications