Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 7, Pages 3897-3905Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00244
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Funding
- Strategic Priority Research Program of CAS [XDB14040201]
- NNSFC projects [21402192, 21672255, 21621064]
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An effective one-pot procedure for enantiomerical synthesis of thiazole-containing amino acid (TCAA) has been established via a cascade disulfide cleavage/thiocarbonylation/intramolecular Staudinger reduction/aza-Wittig/oxidation reaction. Starting from the commercially available amino acid building blocks, a number of TCAAs were prepared in good yields and with excellent optical purities. This method bears features of mild reaction conditions, wide substrate adaptability, and good functional group tolerance. The power of this method was also demonstrated through the concise total synthesis of cyclic hexapeptide Venturamides A and B.
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