Synthesis of Iriomoteolide-1a C13−C23 Fragment via Asymmetric Conjugate Addition and Julia−Kocienski Coupling Reaction
Yen-Jin Chin
Shun-Yi Wang
Teck-Peng Loh
10.1021/ol901480s.s001
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Iriomoteolide_1a_C13_C23_Fragment_via_Asymmetric_Conjugate_Addition_and_Julia_Kocienski_Coupling_Reaction/2834320
The key C13−C23 fragment toward the total synthesis of iriomoteolide-1a (<b>1</b>) has been constructed from an 1,2-acetonide containing aldehyde <b>5</b> via a Julia−Kocienski olefination with the C16−C23 segment <b>6</b>. 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.
2009-08-20 00:00:00
methylmagnesium bromide
6.
olefination
aldehyde 5
Fragment
ester
Asymmetric Conjugate Addition
stereoselective introduction
acetonide
synthesis
Iriomoteolide
fragment
conjugate addition
iriomoteolide
Julia
Synthesi
C 29 methyl group