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• W2067614973 startingPage "495" @default.
• W2067614973 abstract "The total syntheses of naturally occurring bis- and tris(heterocyclic)cyclopeptide bistratamides J (1), H (2), and E (3) from two types of dehydropeptides are described. The strategy involves the preparation of the promising building blocks: N-{2-[(S)-1-(N-benzyloxycarbonyl)amino-2-methylpropyl]thiazol-4-ylcarbonyl}-L-Val-(S)NH2 (4) as the left-half component, and methyl N-(3-bromo-2-oxopropanoyl)-L-Val-O-(tert-butyldiphenylsilyl)-L-threonate (5) as the right-half. The subsequent Hantzsch thiazole synthesis between 4 and 5 afforded a linear N,O-protected bis(heterocyclic)peptide as the precursor of 1. Upon deprotection, the precursor was converted to 1 via macrocyclization under high-dilution condition, using BOP [benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate] as the condensing agent. Furthermore, 1 was converted to 2, which was transformed into 3 via ring-opening and re-oxazolination." @default.
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• W2067614973 date "2008-04-15" @default.
• W2067614973 modified "2023-10-16" @default.
• W2067614973 title "Total Syntheses of Bistratamides J, E, and H from Two Types of ΔAla-Containing Oligopeptides" @default.
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• W2067614973 doi "https://doi.org/10.1246/bcsj.81.495" @default.
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