Total Synthesis of Lophirone F Hexamethyl Ether

Le, Hoang M.; Mac, Hung D.; Oh, Chang Ho; Dd, Do

doi:10.1002/ejoc.201801827

Cited by 3 publications

(1 citation statement)

References 49 publications

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“…The successful realization of such a reaction would lead to spirocyclic scaffolds, which are aimed at by medicinal chemistry and, as previously pointed out, are much underexplored. Previous works on D–A cyclopropane cycloaddition were mostly directed at a natural bioactive 2,5-cis-substituted tetrahydrofuran motif with hydroxylated aryl substituents of lignans. , Herein we are able obtain compounds that are similar but contain an extra incorporation of a pharmacophoric unit of imidazol-5-one, which is present in the medications Loprazolam and Irbesartan.…”

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confidence: 99%

Imidazol-5-one as an Acceptor in Donor–Acceptor Cyclopropanes: Cycloaddition with Aldehydes

et al. 2020

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Spiro[imidazol-5-one-4,1′-cyclopropanes] behave as donor–acceptor (D–A) cyclopropanes in a formal cycloaddition reaction with aldehydes. The activation of such type of cyclopropanes is achieved with an equivalent of Brønsted acid. The reaction proceeds in high yields of 51–92% and demonstrates moderate diastereoselectivity at the quaternary stereocenter, which is determined by the electron-donating nature of the aldehyde partner. The ease of separation of stereoisomers allowed the creation of a library of 44 spiroannulated tetrahydrofurans with various substitution patterns.

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confidence: 99%