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Journal Article
Research Support, Non-U.S. Gov't
A Bioinspired Cascade Sequence Enables Facile Assembly of Methanodibenzo[b,f][1,5]dioxocin Flavonoid Scaffold.
Organic Letters 2018 Februrary 3
A remarkable bioinspired EDDA-mediated method for the selective construction of biologically interesting and highly strained bridged methanodibenzo[b,f][1,5]dioxocin flavonoid scaffold was uncovered by starting from a variety of readily available acylphloroglucinol and 2-hydroxycinnamaldehyde substrates. This method merges a fascinating olefin isomerization/hemiacetallization/dehydration/[3 + 3]-type cycloaddition cascade reaction driven by an in situ generated chromenylium intermediate and provides a convenient and viable synthetic strategy for the efficient access of such flavonoid analogues.
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