ArticleJournal of the American Chemical Society2012
Simultaneous synthesis of both rings of chromenes via a benzannulation/o-quinone methide formation/electrocyclization cascade.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 78 citations in OpenAlex.
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- Synthesis of fused-ring systems and diarylmethane flavonoidsRSC advances · 2025Article
- Gambogic acid: Multi-gram scale isolation, stereochemical erosion toward epi-gambogic acid and biological profile.Frontiers in natural products · 2022Article
- Straightforward Synthesis of Bifunctional Phosphorus Phenols via Phosphination of In Situ GeneratedMolecules (Basel, Switzerland) · 2018Article
- Metalloradical approach to 2H-chromenes.Journal of the American Chemical Society · 2014Article
- Nickel-catalyzed cross-coupling of chromene acetals and boronic acids.Organic letters · 2012Article
- Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels-Alder reactions.Beilstein journal of organic chemistry · 2012Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
A new route to the chromene ring system has been developed which involves the reaction of an α,β-unsaturated Fischer carbene complex of chromium with a propargyl ether bearing an alkenyl group on the propargylic carbon. This transformation involves a cascade of reactions that begins with a benzannulation reaction and is followed by the formation of an o-quinone methide, and finally results in the emergence of a chromene upon an electrocyclization. This reaction was extended to provide access by employing an aryl carbene complex. This constitutes the first synthesis of chromenes in which both rings of the chromene system are generated in a single step and is highlighted in the synthesis of lapachenole and vitamin E.
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Registered trials
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