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- W2500363721 abstract "The enantiospecific total synthesis of erythronolide A (1) through (9S)-9-deoxo-9-hydroxyerythronolide A (2) from the chiral C1–C6, C7–C9, and C10–C13 synthetic segments is described. The C10–C13 segment, (3R,4R,5R)-5-O-benzyl-2-iodo-3,4-O-isopropylidene-4-methyl-1-heptene-3,4,5-triol (11) was synthesized in 16 steps and an 8.3% overall yield from D-ribose. The C7–C9 segment, (S)-(+)-2-(2-bromo-1-methylethyl)-1,3-dioxolane (47) was prepared from methyl (S)-(+)-3-hydroxy-2-methylpropionate in 8 steps and a 49% overall yield. The coupling of the Grignard reagent, prepared from magnesium and 47, and the C1–C6 segment, 3,5,7-tri-O-benzyl-1,4,6-trideoxy-4,6-di-C-methyl-keto-L-ido-2-heptulose (13), afforded 5,7,9-tri-O-benzyl-2,3,6,8-tetradeoxy-2,4,6,8-tetra-C-methyl-L-threo-L-ido-nonose ethylene acetal (48) and its C4-epimer in 79% and 8% yields, respectively. 5,7,9-Tri-O-benzyl-4-O-t-butyldimethylsilyl-2,3,6,8-tetradeoxy-2,4,6,8-tetra-C-methyl-L-threo-L-ido-nonose (12), derived from 48, was subjected to coupl..." @default.
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- W2500363721 date "1989-08-01" @default.
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- W2500363721 title "Total Synthesis of Erythronolide A" @default.
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