A gram-scale synthesis of lachnanthocarpone

A gram-scale synthesis of lachnanthocarpone

[Display omitted] The synthesis of lachnanthocarpone (2,6-dihydroxy-9-phenyl-1H-phenalen-1-one, 1), a powerful antioxidant from Lachnanthes tinctoria (Haemodoraceae), has been re-examined to extend the amount of material that can be prepared. Including a Buchwald hydroxylation into the synthetic pla...

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Veröffentlicht in:Results in Chemistry 2024-01, Vol.7, p.101404, Article 101404
Hauptverfasser: Salazar, Andrea, Otálvaro, Felipe
Format: Artikel
Sprache:eng
Schlagworte:
Buchwald aromatic substitution
Microwave-assisted synthesis
Phenylphenalenones
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Zusammenfassung:[Display omitted] The synthesis of lachnanthocarpone (2,6-dihydroxy-9-phenyl-1H-phenalen-1-one, 1), a powerful antioxidant from Lachnanthes tinctoria (Haemodoraceae), has been re-examined to extend the amount of material that can be prepared. Including a Buchwald hydroxylation into the synthetic plan in conjunction with microwave assistance allowed the preparation of 3.5 g of material in seven steps (22 % global yield), transforming this synthesis into the most efficient hitherto.
ISSN:2211-7156
2211-7156
DOI:10.1016/j.rechem.2024.101404