Total synthesis of cyclodepsipeptide Hikiamides <b> A</b>-<b>C</b>

FU Donglin; RAO Xuemin; XU Jinyi; XIE Weijia; WU Xiaoming

doi:10.11665/j.issn.1000-5048.20180207

Journal of China Pharmaceutical University > 2018 > 49(2): 181-186. > DOI: 10.11665/j.issn.1000-5048.20180207

FU Donglin, RAO Xuemin, XU Jinyi, XIE Weijia, WU Xiaoming. Total synthesis of cyclodepsipeptide Hikiamides A-C[J]. Journal of China Pharmaceutical University, 2018, 49(2): 181-186. DOI: 10.11665/j.issn.1000-5048.20180207

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Total synthesis of cyclodepsipeptide Hikiamides A-C

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Total synthesis of cyclodepsipeptide Hikiamides A - C was described. Fragment convergent condensation method was applied for the preparation of Hikiamides A - C , starting from Commercially available amino acid such as L-N-Boc-Phe-OH, L-N-Boc-Trp-OH, L-N-Cbz-Van-OH etc. Tripeptide fragments(compounds 5a / 5b )and dipeptide fragments(compounds 8a / 8b )were first prepared. The subsequent condensation of the resulted two fragments provided protected linear pentapetides(compounds 9a / 9b / 9c ); Finally, the linear pentapetide was cyclized by a mixed condensing agents comprised of PyBOP and HBTU. Hikiamides A - C was obtained with total yields of 9%, 11% and 6. 5%, respectively. Compared with the natural source, this method has the advantages of low cost, convenient operation and high yield, which effectively solves the problem of low isolated yield of Hikiamides A - C from Fusarium sp.
- Fusarium sp.,
- cyclodepsipeptide,
- Hikiamides A-C,
- PPARγ,
- natural products,
- total synthesis

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