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Functionalization of 3,5,6‐trialkyl‐4‐hydroxy‐2‐pyrones in the 6‐α position
Author(s) -
Köster Gerhard,
Hoffmann Reinhard W.
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870859
Subject(s) - chemistry , substituent , surface modification , bromide , ketone , alcohol , pyrone , organic chemistry
The preparation of 6‐ethyl‐4‐hydroxy‐3,5‐dimethyl‐2‐pyrone ( 5 ) has been improved. Selective functionalization in the 6‐α position of the pyrone 5 was possible by converting it into the 4‐acetoxy compound 11 followed by selenium dioxide oxidation to the alcohol 13 . The latter could be oxidized to the ketone 17 or be converted via the bromide 12 into other 2‐pyrones having a hetero substituent in the 6‐α position.