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Lead Tetraacetate Oxidation on Caryachine, A Phenolic Pavine
Author(s) -
Chiou ChiMing,
Lee ShoeiSheng
Publication year - 1997
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.199700058
Subject(s) - chemistry , dichloromethane , group (periodic table) , phenols , organic chemistry , position (finance) , alkaloid , medicinal chemistry , stereochemistry , solvent , finance , economics
Lead tetraacetate oxidation on caryachine, a pavine alkaloid possessing a phenolic group at the position para to the N ‐methine, in dichloromethane yielded four products — 10‐acetoxy‐ O ‐acetyl‐caryachine, 10‐acetoxycaryachine, 7‐acetoxy‐ O ‐acetylcaryachine and (6 S , 11 R , 12 R )‐11‐acetoxy‐ O ‐acetyl‐caryachine. The reaction took place via adoption of an acetoxy group at a position majorly ortho to the phenolic group, but very minorly at the desired benzylic position para to the phenolic group.