The synthesis of 7,9-dimethoxy-3-propyl-3,4-dihydro-1H-benzo[g]isochromene1,5,10-trione: A potential monomer for the synthesis of the natural product xylindein

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dc.contributor.authorHossain, Md. Firoj
dc.contributor.authorLemmerer, Andreas
dc.contributor.authorde Koning, Charles B
dc.date.accessioned2020-12-01T10:15:07Z
dc.date.available2020-12-01T10:15:07Z
dc.date.issued2020
dc.description.abstractA novel synthesis of a 3-propyl-substituted-benzo[g]isochromene quinone, a potential monomer of the natural product xylindein, was accomplished in 9 steps (overall yield of 8.2%) from 2,4- dimethoxybenzaldehyde. Key steps included the use of a cross-metathesis reaction in which ethyl-3-allyl-4- (benzyloxy)-1,6,8-trimethoxy-2-naphthoate was converted into ethyl-4-(benzyloxy)-1,6,8-trimethoxy-3-(4- oxopent-2-enyl)-2-naphthoate as a mixture of (E)- and (Z)-isomers. Following an oxa-Michael addition reaction, a racemic mixture of the desired product, 5-(benzyloxy)-7,9,10-trimethoxy-3-(2-oxopropyl)-3,4- dihydro-1H-benzo[g]isochromen-1-one, the basic xylindein lactone skeleton, was obtained.en_US
dc.identifier.citationHossain, Md. F. et al . (2020). The synthesis of 7,9-dimethoxy-3-propyl-3,4-dihydro-1H benzo[g]isochromene1,5,10-trione: A potential monomer for the synthesis of the natural product xylindein. Arkivoc , part v, 0-0en_US
dc.identifier.issn15517004
dc.identifier.uri10.24820/ark.5550190.p011.313
dc.identifier.urihttp://hdl.handle.net/10566/5467
dc.language.isoenen_US
dc.publisherArkivocen_US
dc.subjectXylindeinen_US
dc.subjectChemistryen_US
dc.subjectBenzo[g]isochromene quinoneen_US
dc.subjectCross-metathesisen_US
dc.titleThe synthesis of 7,9-dimethoxy-3-propyl-3,4-dihydro-1H-benzo[g]isochromene1,5,10-trione: A potential monomer for the synthesis of the natural product xylindeinen_US
dc.typeArticleen_US

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