“…Rodrigo and coworkers have observed that diester monoreduction may be used in I-arylnaphthalide lignan synthesis. 49 Reductions in THF may be catalyzed by sodium borohydride (5 mol %).50 Various borane derivatives have been employed in ester reduction. BH3·NHPh2 has been used to reduce aliphatic esters, although aromatic esters are not readily reduced.…”
Section: Reductions Using Metal Hydride Reagentsmentioning
“…Rodrigo and coworkers have observed that diester monoreduction may be used in I-arylnaphthalide lignan synthesis. 49 Reductions in THF may be catalyzed by sodium borohydride (5 mol %).50 Various borane derivatives have been employed in ester reduction. BH3·NHPh2 has been used to reduce aliphatic esters, although aromatic esters are not readily reduced.…”
Section: Reductions Using Metal Hydride Reagentsmentioning
Novel routes to 1 -aryl-5,6-dialkoxy-l,3-dihydrobenzo[cJthiophene 2'2-dioxides (1 3) and to the corresponding benzo[c]furan (8) have been developed; these species yield quinodimethanes (1 2) via thermal extrusion of SO, and isobenzofurans (5c) in an acid-catalysed process, respectively, which then react with various dienophiles to provide structural analogues of the aryltetralin and arylnaphthalene lignans.
OMe
“…The double Stobbe condensation of a succinic diester with an aromatic aldehyde is a useful synthetic route for the construction of the basic lignan skeleton. [1][2][3][4][5][6][7] Two successive Stobbe condensation reactions of a succinate diester with an aromatic aldehyde generates an (E,E)-dibenzylidenesuccinate (Scheme 1) that is found in naturally occurring lignans such as phebalarin, 8 jatrodien, 9 and taiwanin. 10…”
The development of new methods for lignan synthesis is reported. A recently reported method for the preparation of 1-aryl-1,2-dihydronaphthalenes is exploited to prepare magnoshinin, a naturally occurring lignan, and cyclogalgravin (3,4-dehydrogalbulin), a derivative of a natural lignan.
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