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Synthesis of 3-benzylidene-dihydrofurochromen-2-ones: promising intermediates for biflavonoid synthesis.

ABSTRACT: A route to 3-benzylidene dihydrofurochromen-2-ones from 2H-chromenes is described. Lactonization of 2H-chromenes was achieved using a two-step cyclopropanation-rearrangement sequence. Subsequent conversion of these intermediates to the corresponding ?-benzylidene lactones was achieved by lithium enolate Aldol reaction, followed by base-promoted elimination of the aldolate mesylates. The alkene geometry was found to be base-dependent. While KO t Bu favored formation of the E-isomer, DBU showed a slight preference for the Z-isomer. In further studies, these 3-benzylidene dihydrofurochromen-2-ones were converted to polyaromatic structures possessing all the required functionality for biflavonoid synthesis.

SUBMITTER: Baron V

PROVIDER: S-EPMC5006937 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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Synthesis of 3-benzylidene-dihydrofurochromen-2-ones: promising intermediates for biflavonoid synthesis.

Baron Verna V Mead Keith T KT

Heterocyclic communications 20150725 4

A route to 3-benzylidene dihydrofurochromen-2-ones from 2H-chromenes is described. Lactonization of 2H-chromenes was achieved using a two-step cyclopropanation-rearrangement sequence. Subsequent conversion of these intermediates to the corresponding α-benzylidene lactones was achieved by lithium enolate Aldol reaction, followed by base-promoted elimination of the aldolate mesylates. The alkene geometry was found to be base-dependent. While KO t Bu favored formatio ...[more]

PMID: 27594762

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