Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 19, Issue 3, Pages 738-741Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2008.12.022
Keywords
Bisbibenzyl; Riccardin C; LXRs; Agonist; Synthesis; Structure-activity relationship; Suzuki-Miyaura coupling
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Funding
- Ministry of Education, Culture, Sports, Science, and Technology of the Japanese Government [18590113]
- Grants-in-Aid for Scientific Research [18590113] Funding Source: KAKEN
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Riccardin C, a nuclear receptor LXR alpha selective agonist, is an 18-membered macrocyclic bisbibenzyl isolated from several liverworts. Synthesis of riccardin C and its seven O-methylated derivatives was accomplished. The synthetic sequence highlights an intramolecular Suzuki-Miyaura coupling in the formation of the 18-membered biaryl linkage present in riccardin C. The structure-activity relationship of these compounds suggests that all of the phenolic hydroxy groups present in riccardin C are essential for the activation of LXRa. (C) 2008 Elsevier Ltd. All rights reserved.
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