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. 2023 Jan;37(1):56-62.
doi: 10.1080/14786419.2021.1948843. Epub 2021 Jul 6.

The efficient synthesis and biological evaluation of justicidin B

Taejung Kim  1 , Young-Joo Kim  1 , Kyu-Hyuk Jeong  1 , Young-Tae Park  1 , Hyukjoon Kwon  1 , Pilju Choi  1 , Ha-Neul Ju  1 , Cheol Hee Yoon  1 , Ji-Yool Kim  1   2 , Jungyeob Ham  1   2
Affiliations

The efficient synthesis and biological evaluation of justicidin B

Taejung Kim et al. Nat Prod Res. 2023 Jan.

Abstract

A facile new synthetic method for the preparation of a Type-A 1-arylnaphthalene lactone skeleton was developed and used to synthesise justicidin B and several derivatives. Key synthesis steps included Hauser-Kraus annulation of a phthalide intermediate and Suzuki-Miyaura cross coupling between a triflated naphthalene lactone intermediate and various potassium organotrifluoroborates. With two exceptions, the derivatives showed significant inhibitory effect on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in mouse macrophages. Moreover, several compounds, including justicidin B, had marked cytotoxicity towards six human tumour cell lines.

Keywords: Justicidin B; annulation; cross coupling; natural products; total synthesis.

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