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- W1987840621 abstract "Abstract In the presence of sulfur dioxide and an acid promoter, (−)‐(1 E ,3 Z )‐2‐methyl‐1‐((1 S )‐1‐phenylethoxy)penta‐1,3‐dien‐3‐yl isobutyrate reacts with ( Z )‐3‐(trimethylsilyloxy)pent‐2‐ene giving a silyl sulfinate intermediate that undergoes, in the presence of palladium catalyst, a desilylation and retro‐ene elimination of SO 2 with formation of (−)‐(1 Z ,2 S ,3 R ,4 S )‐1‐ethylidene‐2,4‐dimethyl‐5‐oxo‐3‐((1 S )‐1‐phenylethoxy)‐heptyl isobutyrate as major product. This ethyl ketone undergoes cross‐aldol reaction with (2 S )‐2‐methyl‐3‐[( tert ‐butyldimethylsilyl)oxy]propanal giving an aldol that is reduced into a stereoheptad corresponding to the C(19)‐C(27)‐segment of Rifamycins with high diastereoselectivity and enantiomeric excess." @default.
- W1987840621 created "2016-06-24" @default.
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- W1987840621 date "2004-12-29" @default.
- W1987840621 modified "2023-10-17" @default.
- W1987840621 title "Expeditious Asymmetric Synthesis of a Stereoheptad Corresponding to the C(19)-C(27)-Ansa Chain of Rifamycins: Formal Total Synthesis of Rifamycin S" @default.
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- W1987840621 doi "https://doi.org/10.1002/chem.200400825" @default.
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