Journal of Organic Chemistry p. 2260 - 2267 (1981)
Update date:2022-08-05
Topics:
Sandifer, Ronda M.
Bhattacharya, Ajit K.
Harris, Thomas M.
The dianion (2) of 2,4-pentanedione and the trianion (10) of 2,4,6-heptanetrione were acylated by lithium salts of the unprotected hydroxybenzoates methyl 2-hydroxy-4-methoxy-6-methylbenzoate (1b), methyl 2,6-dihydroxy-4-methoxybenzoate (7b), and methyl 2,4-dimethoxy-6-hydroxybenzoate (7c), as well as by the alkoxybenzoates methyl 2,4,6-trimethoxybenzoate (7d) and methyl 2,4,6-tribenzoxybenzoate (7e).The aryl 1,3,5,7-octanetetraones (11b-d and 12) resulting from acylation of 10 were cyclized in biomimetic processes to naturally occurring benzophenones and xanthones.Hydrogenolysis of 1-(2,4,6-tribenzoxyphenyl)-1,3,5,7-octanetetraone (11e) and cyclization gave norlichexanthone (20).
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