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Acid‐Catalyzed Regiodivergent Annulation of 4‐Hydroxycoumarins with Isoprene: Entry to Pyranocoumarins and Pyranochromones
Author(s) -
Li Ying,
Hu YanCheng,
Zheng Hao,
Ji DingWei,
Cong YuFeng,
Chen QingAn
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901154
Subject(s) - annulation , chemistry , isoprene , lewis acids and bases , catalysis , combinatorial chemistry , substrate (aquarium) , organic chemistry , stereochemistry , oceanography , copolymer , geology , polymer
An acid‐catalyzed regiodivergent formal [3+3] annulation of 4‐hydroxycoumarins with isoprene is developed. A variety of pyranocoumarins were obtained exclusively in the presence of strong Brønsted acid, while varying to Lewis acid delivered pyranochromones as main products. The protocol also features high atom‐economy, wide substrate scope, easy scale‐up, and good applications in natural product synthesis.