Journal
ORGANIC LETTERS
Volume 23, Issue 21, Pages 8380-8384Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03120
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Funding
- Key Program of the National Natural Science Foundation of China [22137008]
- Yunnan Wanren Project [YNWR-KJLJ-2019-002]
- Youth Innovation Promotion Association, CAS [2020386]
- Reserve Talents of Young and Middle-aged Academic and Technical Leaders in Yunnan Province
- State Key Laboratory of Phytochemistry and Plant Resources in West China [P2021-ZZ06]
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The biomimetic synthesis from arglabin led to the successful production of guaianolide dimers, trimers, and tetramers, with the trimer showing stronger anti-hepatoma cytotoxicity than sorafenib.
The biomimetic synthesis of guaianolide dialers lavandiolides H, I, and K and artematrolide F containing a spirolactone moiety has been accomplished for the first time from naturally abundant arglabin in four to six steps with an overall yield up to 60%, and a series of natural product-like guaianolide dimers, trimer, and tetramer were also successfully synthesized. Notably, the trimeric compound exhibited antihepatoma cytotoxicity more potent than that of sorafenib with IC50 values of 6.2 mu M (HepG2), 6.8 mu M (Huh7), and 7.2 mu M (SK-HEP-1).
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