Concise Synthesis of Chafurosides A and B

Concise Synthesis of Chafurosides A and B

The regioselective synthesis of chafurosides A (1) and B (2) from the same methyl ketone 5 was accomplished using a novel protecting group strategy. Both flavone rings were constructed from β-diketone intermediate 4, which was readily obtained by condensation of an acyl donor and ketone 5. Construct...

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Veröffentlicht in:Organic letters 2009-06, Vol.11 (11), p.2233-2236
Hauptverfasser: Furuta, Takumi, Nakayama, Miho, Suzuki, Hirotaka, Tajimi, Hiroko, Inai, Makoto, Nukaya, Haruo, Wakimoto, Toshiyuki, Kan, Toshiyuki
Format: Artikel
Sprache:eng
Schlagworte:
Flavones - chemical synthesis
Flavones - chemistry
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Ketones - chemistry
Molecular Structure
Stereoisomerism
Tea - chemistry
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Beschreibung
Zusammenfassung:The regioselective synthesis of chafurosides A (1) and B (2) from the same methyl ketone 5 was accomplished using a novel protecting group strategy. Both flavone rings were constructed from β-diketone intermediate 4, which was readily obtained by condensation of an acyl donor and ketone 5. Construction of the dihydrofuran ring was achieved via an intramolecular Mitsunobu reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol900689m