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Unexpected regioselectivity in the photocyclization of a chiral 2,3-bisbenzylidenesuccinate, leading to a podophyllotoxin related cyclolignan

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dc.abstract.enThe Stobbe condensation between 3′,4′,5′-trimethoxyacetophenone and a benzylidenesuccinate derived from piperonal gave the Z,E-2,3-bisbenzylidenesuccinate as the only product. Such regioselectivity was explained by considering the Newman’s projections of the transition states of this reaction. Introducing L-prolinol as a chiral auxiliary, macrolactonization and subsequent photocyclization of the atropoisomeric cyclic amide ester led to new cyclolignan analogue. By comparing the regioselectivity observed in this study with our previous results, some general rules regarding the photocyclization of chiral 2,3-bisbenzylidenesuccinates could be established.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorCzarnocki, Zbigniew
dc.contributor.authorMaurin, Jan
dc.contributor.authorKrawczyk, Krzysztof
dc.contributor.authorRoszkowski, Piotr
dc.contributor.authorLisiecki, Kamil
dc.date.accessioned2024-01-26T11:19:15Z
dc.date.available2024-01-26T11:19:15Z
dc.date.issued2018
dc.description.financeNie dotyczy
dc.description.volume364
dc.identifier.doi10.1016/J.JPHOTOCHEM.2018.06.023
dc.identifier.issn1010-6030
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/124176
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Photochemistry and Photobiology A: Chemistry
dc.relation.pages297-302
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.enLignans podophyllotoxi photocyclization l-prolinol Stobbe condensation
dc.titleUnexpected regioselectivity in the photocyclization of a chiral 2,3-bisbenzylidenesuccinate, leading to a podophyllotoxin related cyclolignan
dc.typeJournalArticle
dspace.entity.typePublication