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J Org Chem. 2018 Apr 6;83(7):3897-3905. doi: 10.1021/acs.joc.8b00244. Epub 2018 Mar 19.

One-Pot Enantiomeric Synthesis of Thiazole-Containing Amino Acids: Total Synthesis of Venturamides A and B.

Liu Y1,2, He P1,3, Zhang Y1,3, Zhang X2, Liu J1, Du Y1,3.

Author information

1
State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences , Chinese Academy of Sciences , Beijing 100085 , China.
2
School of Chemistry and Chemical Engineering , Yantai University , Yantai 264005 , China.
3
School of Chemistry and Chemical Engineering , University of Chinese Academy of Sciences , Beijing 100049 , China.

Abstract

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.

PMID:
29533619
DOI:
10.1021/acs.joc.8b00244
[Indexed for MEDLINE]

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