Open AccessSynthetic Studies toward the Hamigerans with a 6–7–5 Tricyclic Core
Author(s) -
Baiyang Jiang,
Mingji Dai
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c01253
Subject(s) - chemistry , aryne , ring (chemistry) , tricyclic , isopropyl , conjugate , quaternary carbon , stereochemistry , carbon skeleton , suzuki reaction , core (optical fiber) , medicinal chemistry , combinatorial chemistry , catalysis , organic chemistry , enantioselective synthesis , mathematical analysis , palladium , materials science , mathematics , composite material
An approach toward the 6-7-5 tricyclic carbon skeleton of the hamigeran natural products was developed. The key steps include a benzyne-β-ketoester annulative ring expansion to form the 7-membered ring, a Nazarov reaction to form the 5-membered ring, a Ni-catalyzed conjugate methyl addition or a Corey-Chaykovsky reaction to install the all-carbon quaternary center, and a Suzuki cross coupling followed by reduction to introduce the isopropyl group.