%0 Generic
%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/dataset/Synthesis_of_Iriomoteolide_1a_C13_C23_Fragment_via_Asymmetric_Conjugate_Addition_and_Julia_Kocienski_Coupling_Reaction/2834323
%R 10.1021/ol901480s.s002
%2 https://acs.figshare.com/ndownloader/files/4532020
%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