131086-91-4Relevant articles and documents
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
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.