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- W2951170025 abstract "The highly stereoselective total synthesis of the macrolide antibiotic, bafilomycin A1 (1), the first specific potent inhibitor of vacuolar H+-ATPase, has been achieved by a convergent route involving the synthesis and coupling of its 16-membered tetraenic lactone and β-hydroxyl hemiacetal side-chain subunits. The C1−C17 16-membered lactone aldehyde 2 was synthesized through the coupling of the C5−C11 vinyl iodide 4 and the C12−C17 vinylstannane 5, followed by construction of the C1−C4 diene and macrolactonization. The aldol coupling of 2 and the C18−C25 ethyl ketone 3 followed by desilylation provided 1, which was identical with natural bafilomycin A1. The key synthetic segments 3−5 were effectively synthesized from the readily available chiral materials, d-glucose, ethyl (S)-lactate, and methyl (S)-3-hydroxy-2-methylpropionate, respectively." @default.
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- W2951170025 date "2010-08-03" @default.
- W2951170025 modified "2023-09-27" @default.
- W2951170025 title "ChemInform Abstract: Total Synthesis of Bafilomycin A1." @default.
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- W2951170025 doi "https://doi.org/10.1002/chin.199738289" @default.
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