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Indium‐promoted Conversion of Allylic Bromide to Alcohol Moiety and Synthesis of Pipermethystine Skeletons
Author(s) -
Liou BoSian,
Chou ShangShing Peter
Publication year - 2016
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201600239
Subject(s) - chemistry , indium , moiety , bromide , yield (engineering) , alcohol , allylic rearrangement , allylic alcohol , organic chemistry , derivative (finance) , natural product , combinatorial chemistry , medicinal chemistry , catalysis , materials science , economics , financial economics , metallurgy
Dihydropyridone bromide ( 2 ) was converted to the corresponding alcohol ( 1 ) by reaction with indium in air or with indium followed by treatment with a sulfonyloxaziridine. The alcohol ( 1 ) was transformed in four steps to a phenylsulfone‐substituted pipermethystine derivative ( 10 ). Reductive cleavage of the phenylsulfone did not yield the pipermethystine natural product. Several new pyridone derivatives were synthesized.