131086-91-4Relevant academic research and scientific papers
Ortho and remote metalation - cross coupling strategies. Total synthesis of the naturally occurring fluorenone dengibsinin and the azafluoranthene alkaloid imeluteine
Fu,Zhao,Sharp,Snieckus
, p. 227 - 236 (2007/10/02)
The total synthesis of the naturally occurring fluorenone, dengibsinin (7a), and the azafluoranthene alkaloid, imeluteine (30e), is described. Using combined ortho metalation - cross coupling sequences that terminate in Friedel-Crafts (18b→6d) and remote
Ellagic acid analogues
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, (2008/06/13)
Synthetic novel ellagic acid congeners of the formula: STR1 wherein: R1 is --H, --OH or --OR'; R2 is --H, --OH or --OR'; R3 is --H, --OH or --OR'; R4 is --H, --OH or --OR'; R5 is --H, --OH or --OR'; R6 is --H, --OH or --OR'; R' is lower alkyl having 1 to 8 carbon atoms or --CH2 --Ar; Ar is phenyl or substituted phenyl, and at least one of R1, R2, R3, R4, R5 and R6 is other than --H. The above compounds and 6H-dibenzo[b,d]pyran-6-one are useful for inhibiting mutagenic activity in living cells.
Sequential Directed Ortho Metalation-Boronic Acid Cross-Coupling Reactions. A General Regiospecific Route to Oxygenated Dibenzopyran-6-ones Related to Ellagic Acid
Alo, B. I.,Kandil, A.,Patil, P. A.,Sharp, M. J.,Siddiqui, M. A.,et al.
, p. 3763 - 3768 (2007/10/02)
A general regiospecific synthesis of dibenzopyran-6-one derivatives 1a,c and 8a-i related to ellagic acid is described (Scheme I, Table I).The sequence involves directed ortho metalation-boronation of benzamides 4 to give the arylboronic acids 5, which, upon palladium-catalyzed cross-coupling with alkoxybromobenzenes 6 leads to the biphenylamides 7.BBr3 demethylation followed by acid-catalyzed cyclization affords pyranone 8.In this manner, the naturally occurring dibenzopyranones 1a, autumnariol (1c), and the heterocyclic analogue 13 (Scheme III) were efficiently prepared.
