Open AccessCatalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones
Author(s) -
Xinpei Cai,
Weiguang Liang,
Mingxin Liu,
Xiating Li,
Mingji Dai
Publication year - 2020
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.0c06179
Subject(s) - bicyclic molecule , chemistry , carbonylation , tetrahydropyran , lactone , catalysis , tetrahydrofuran , ring (chemistry) , palladium , combinatorial chemistry , stereochemistry , organic chemistry , carbon monoxide , solvent
A novel palladium-catalyzed ring opening carbonylative lactonization of readily available hydroxycyclopropanols was developed to efficiently synthesize tetrahydrofuran (THF) or tetrahydropyran (THP)-fused bicyclic γ-lactones, two privileged scaffolds often found in natural products. The reaction features mild reaction conditions, good functional group tolerability, and scalability. Its application was demonstrated in a short total synthesis of (±)-paeonilide. The fused bicyclic γ-lactone products can be easily diversified to other medicinally important scaffolds, which further broadens the application of this new carbonylation method.