Synthesis of Louisianin C

Synthesis of Louisianin C

The synthesis of louisianin C (3), a member of a small family of 3,4,5-trisubstituted pyridyl natural products, is achieved in six steps and 11% overall yield starting from commercially available 3,5-dibromopyridine. The key step is a fluoride-induced desilylation−cyclization to afford carbinol 12....

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Veröffentlicht in:Journal of organic chemistry 2003-06, Vol.68 (12), p.4970-4972
Hauptverfasser: Beierle, John M, Osimboni, Ekundayo B, Metallinos, Costa, Zhao, Yajun, Kelly, T. Ross
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - analysis
Alkaloids - chemical synthesis
Allyl Compounds - analysis
Allyl Compounds - chemical synthesis
Catalysis
Chemistry
Cyclization
Exact sciences and technology
Fluorides - chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Molecular Structure
Organic chemistry
Preparations and properties
Pyridines - analysis
Pyridines - chemical synthesis
Silanes - chemistry
Streptomyces - chemistry
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Beschreibung
Zusammenfassung:The synthesis of louisianin C (3), a member of a small family of 3,4,5-trisubstituted pyridyl natural products, is achieved in six steps and 11% overall yield starting from commercially available 3,5-dibromopyridine. The key step is a fluoride-induced desilylation−cyclization to afford carbinol 12.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0341618