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A method for the facile synthesis of ring-A hydroxylated flavones

✍ Scribed by Mark Cushman; Dhanapalan Nagarathnam

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 235 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)97100-4

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✦ Synopsis

A general method for the facile synthesis of ring-A hydroxylated flavones is described.

Treatment of the hydroxylated acetophenones 6a-d with enough lithium bls(trimethyl)silyl amide to deprotonate all of the phenols as well as to generate the lithium enolate of the ketone, followed by addition of the acid chlorides 7a-d, gave the 1,3-diketones IIa-g, which were cyclixed to the desired products 9a-g in high yield.

Recent interest in ring-A hydroxylated flavones stems from their ability to inhibit retroviral reverse transcriptases,1.2.3 including HIV reverse transcriptase,*v3 as well as their capacity to inhibit protein tyrosine kinases43 and serine/threonine kinases .4 In fact, a naturally occurring ring-A hydroxylated flavone and several related compounds have recently been shown to inhibit HIV-induced syncytium formation.6 In addition, these

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