Chinese Journal of Organic Chemistry Previous Articles     Next Articles

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胭脂酮酸的合成新方法

高鑫a, 张晓莹a, 胡志飞a,*, 曹鸿志a,b,c,*   

  1. a中国海洋大学医药学院 海洋药物教育部重点实验室 山东省糖科学与糖药物重点实验室 青岛 266003;
    b中国海洋大学三亚海洋研究院 三亚 572025;
    c青岛海洋科技中心海洋药物与生物制品实验室 青岛 266237
  • 收稿日期:2026-04-06 修回日期:2026-04-22
  • 基金资助:
    国家重点研发计划(No. 2025YFC3409500)、国家自然科学基金(No. 92478131, 22277111, 22577125)、山东省重点研发计划(重大科技创新工程)(No. 2024CXGC010615)和泰山学者特聘专家(No. TSTP20221114)资助项目

A New Method for the Synthesis of Kermesic Acid

Gao xina, Zhang Xiaoyinga, Hu Zhifeia,*, Cao Hongzhia,b,c,*   

  1. aKey Laboratory of Marine Drugs of Ministry of Education, Shandong Key Laboratory of Glycoscience and Glycotherapeutics, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003;
    bSanya Oceanographic Institute, Ocean University of China, Sanya 572025;
    cLaboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237
  • Received:2026-04-06 Revised:2026-04-22
  • Contact: *E-mail: zfhu@ouc.edu.cn; hzcao@ouc.edu.cn
  • Supported by:
    National Key Research and Development Program of China (No. 2025YFC3409500), the National Natural Science Foundation of China (No. 92478131, 22277111, and 22577125), the Department of Science and Technology of Shandong Province (No. 2024CXGC010615), the Taishan Scholar Project (No. TSTP20221114).

Kermesic acid is an aromatic polyketide primarily isolated from cochineal insects, which has been widely employed as a natural red colorant. In the biosynthetic pathway, glycosylation of kermesic acid yields carminic acid, a compound of significant economic value with broad applications in dyes, cosmetics, food additives, and related industries. Accordingly, kermesic acid has attracted extensive attention as a key intermediate for the synthesis of carminic acid. Herein, we report a new chemical method for the synthesis of kermesic acid. The key steps involve the in situ generation of arynes from bromoarenes followed by cyclization with phthalides, under the action of lithium diisopropylamide (LDA), enabling the rapid construction of the anthraquinone core and the convenient introduction of major functional groups. Subsequent manipulations, including oxidation state adjustment and demethylation, enabled the efficient total synthesis of kermesic acid in 9 steps with an overall yield of 12.5%, providing a crucial material foundation for functional studies of kermesic acid and the development of animal-free carminic acid synthesis.

Key words: kermesic acid, chemical synthesis, aryne-phthalide annulation, carminic acid