Unexpected regioselectivity in the photocyclization of a chiral 2,3-bisbenzylidenesuccinate, leading to a podophyllotoxin related cyclolignan
Sign Up to like & getrecommendations! Published in 2018 at "Journal of Photochemistry and Photobiology A: Chemistry"
DOI: 10.1016/j.jphotochem.2018.06.023
Abstract: Abstract The 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.… read more here.
Keywords: regioselectivity photocyclization; photocyclization chiral; regioselectivity; cyclolignan ... See more keywords
Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold
Sign Up to like & getrecommendations! Published in 2024 at "Beilstein Journal of Organic Chemistry"
DOI: 10.3762/bjoc.20.15
Abstract: The Hock cleavage, which is compatible with tandem processes, was applied to the synthesis of 1-aryltetralines through a one-pot transformation from readily available benzyl(prenyl)malonate substrates. After the photooxygenation of the prenyl moiety, the resulting hydroperoxide… read more here.
Keywords: cyclolignan; friedel crafts; hock; crafts reactions ... See more keywords