Citation: Liu Long, Wang Bo, Bi Cheng, He Gang, Chen Gong. Efficient preparation of β-hydroxy aspartic acid and its derivatives[J]. Chinese Chemical Letters, ;2018, 29(7): 1113-1115. doi: 10.1016/j.cclet.2018.05.012 shu

Efficient preparation of β-hydroxy aspartic acid and its derivatives

Liu Long ^a ,
Wang Bo ^a ,
Bi Cheng ^a ,
He Gang ^a,b ,
Chen Gong ^a,b,,

a.
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China
b.
Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), Tianjin 300071, China

Corresponding author: Chen Gong, gongchen@nankai.edu.cn
Received Date: 4 April 2018
Revised Date: 2 May 2018
Accepted Date: 3 May 2018
Available Online: 5 July 2018

Figures(2)

We report an efficient and practical synthetic route to various properly-protected erythreo-β-OH-Asp compounds, which are key β-branched α-amino acid units in coralmycin A and other peptide natural products. Fmoc and cyclic ketal-protected erythreo-β-OH-Asp 7 is prepared from cheap chiral precursor L-diethyl tartrate in six steps without the need of column purification. The modified form of 7 serves as a versatile precursor to various β-alkoxyl analogs of erythreo-β-OH-Asp. In addition, we successfully performed a model study toward the total synthesis of coralmycin A, featuring a late stage installation of the side chain primary amide group of erythreo-β-OMe-Asn.
- Amino acid,
- Natural product,
- Erythreo-β-OH-Asp,
- Erythreo-β-OMe-Asn,
- Antibiotics
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