Divergent total synthesis of marine meroterpenoids (+)-dysidavarones A–C

• Published in: Chinese chemical letters Vol. 35; no. 3; pp. 108338 - 108342
• Main Authors: Zhang, Qunlong, Kuang, Yang, Chang, Le, Kang, Jingyi, Wang, Bingjian, Chong, Chuanke, Lu, Zhaoyong
• Format: Journal Article
• Language: English
• Published: NEW YORK Elsevier B.V 01.03.2024; Elsevier
• Subjects: Chemistry; Chemistry, Multidisciplinary; Dysidavarones A–C; Meroterpenoid; Natural product; Physical Sciences; Science & Technology; Sesquiterpene quinone; Total synthesis; Natural product; Meroterpenoid; Sesquiterpene quinone; Dysidavarones A–C; Total synthesis; Dysidavarones A-C
• ISSN: 1001-8417; 1878-5964
• DOI: 10.1016/j.cclet.2023.108338

Here, we report a concise and divergent enantioselective total synthesis of marine sesquiterpene quinone meroterpenoids (+)-dysidavarones A–C (1–3) using predysidavarone 6 as a key common intermediate. The highly strained and bridged eight-membered carbocycle of predysidavarone 6 was constructed by a one-pot intermolecular alkylation and intramolecular arylation of Wieland–Miescher ketone derivative 11 and benzyl bromide 12. The total synthesis of (+)-dysidavarones A–C (1–3) was achieved from predysidavarone 6 in a divergent manner by a late-stage introduction of the ethoxy group, which reveals the possible source of the ethoxy group within (+)-dysidavarones A–C (1–3) and provides a late-stage modifiable route for the synthesis of dysidavarone analogs for further anti-cancer activity evaluation. A concise enantioselective total synthesis of marine sesquiterpene quinone meroterpenoids (+)-dysidavarones A–C and “E” was accomplished in a divergent manner from predysidavarone as a key common intermediate. [Display omitted]