Total Synthesis of Hirsutellone B via Ullmann-Type Direct 13-Membered Macrocyclization

Total Synthesis of Hirsutellone B via Ullmann-Type Direct 13-Membered Macrocyclization

Total synthesis of Hirsutellone B has been achieved by a convergent synthetic strategy. This synthesis features direct construction of the highly strained 13-membered macrocycle of Hirsutellone B utilizing the Ullmann-type reaction. To the best of our knowledge, this is the first application of macr...

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Veröffentlicht in:Organic letters 2011-12, Vol.13 (23), p.6268-6271
Hauptverfasser: Uchiro, Hiromi, Kato, Ryo, Arai, Yuuki, Hasegawa, Miki, Kobayakawa, Yu
Format: Artikel
Sprache:eng
Schlagworte:
Antitubercular Agents - chemical synthesis
Antitubercular Agents - chemistry
Antitubercular Agents - pharmacology
Cyclization
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Heterocyclic Compounds, 4 or More Rings - pharmacology
Molecular Structure
Mycobacterium tuberculosis - drug effects
Stereoisomerism
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Zusammenfassung:Total synthesis of Hirsutellone B has been achieved by a convergent synthetic strategy. This synthesis features direct construction of the highly strained 13-membered macrocycle of Hirsutellone B utilizing the Ullmann-type reaction. To the best of our knowledge, this is the first application of macrocyclization utilizing an intramolecular Ullmann-type reaction between an aliphatic alcohol and aryl halide.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol202748e