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- W2952466083 abstract "Abstract A total synthesis of the new thiazoline-based siderophore desferrithiocin 1, isolated from Streptomyces antibioticus, is described. Thus, a concise synthesis of (S)-2-methylcysteine hydrochloride 11 is first developed based on a modification of Seebach's “self-reproduction of chirality” protocol using the thiazolidine intermediate 8 derived from (S)-cysteine and pivaldehyde as a key intermediate. When a solution of (S)-2-methylcysteine hydrochloride is heated with 2-cyano-3-hydroxypyridine in the presence of triethylamine, (S)-desferrithiocin is produced in 97% yield. In a similar manner, use of (R)-2-methylcysteine in a cyclocondensation with 2-cyano-3-hydroxypyridine led to (R)-desferrithiocin, in a similar yield." @default.
- W2952466083 created "2019-06-27" @default.
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- W2952466083 date "2010-08-20" @default.
- W2952466083 modified "2023-09-26" @default.
- W2952466083 title "ChemInform Abstract: Synthesis of the Thiazoline-Based Siderophore (S)-Desferrithiocin." @default.
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- W2952466083 doi "https://doi.org/10.1002/chin.199343255" @default.
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