Use of Fluoroalkyl as a Latent Group for Internal Alkylation: Application to the Synthesis of Bridged Tetrahydrofluorenones

Use of Fluoroalkyl as a Latent Group for Internal Alkylation: Application to the Synthesis of Bridged Tetrahydrofluorenones

Tetrahydrofluorenones which possess a C9a-fluoroalkyl substituent were efficiently converted to tetrahydrofluorenones which contain a ring bridging C9a−C2. Conditions include a stepwise sequence of conversion to an alkyl bromide followed by treatment with base, and a direct cyclization by treatment...

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Veröffentlicht in:Organic letters 2008-07, Vol.10 (14), p.2983-2985
Hauptverfasser: Parker, Jr, Dann L, Fried, Amy K, Meng, Dongfang, Greenlee, Mark L
Format: Artikel
Sprache:eng
Schlagworte:
Alkylation
Bridged-Ring Compounds - chemical synthesis
Catalysis
Cyclization
Estrogen Receptor beta - agonists
Fluorenes - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Molecular Structure
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Zusammenfassung:Tetrahydrofluorenones which possess a C9a-fluoroalkyl substituent were efficiently converted to tetrahydrofluorenones which contain a ring bridging C9a−C2. Conditions include a stepwise sequence of conversion to an alkyl bromide followed by treatment with base, and a direct cyclization by treatment with lithium chloride in DMF heated to 150 °C.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol800971f