Open AccessTotal Synthesis of ent-Plagiochianin B
Author(s) -
Richard K. Jackson,
John L. Wood
Publication year - 2021
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.0c04219
Subject(s) - chemistry , total synthesis , regioselectivity , enantiomer , enantioselective synthesis , olefin fiber , oxidative cleavage , pyridine , natural product , stereochemistry , palladium , cleavage (geology) , combinatorial chemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
An enantioselective total synthesis of plagiochianin B is described that employs (+)-3-carene as its point of departure and delivers the enantiomer of the natural product. Key features of the synthesis include a palladium-mediated regioselective oxidative cleavage of an olefin residing on a pyridine derived from a 6π-azatriene electrocyclization.
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