Total Synthesis of Buergerinin F and Buergerinin G

Total Synthesis of Buergerinin F and Buergerinin G

Syntheses of buergerinin F (1) and buergerinin G (2) were carried out to establish the absolute stereochemistry of these natural products. A linear sequence was used to synthesize 1 in 15 steps and 9% overall yield from thymidine. Subsequent oxidation of 1 with ruthenium tetroxide afforded 2 in 77%...

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Veröffentlicht in:Journal of organic chemistry 2003-05, Vol.68 (10), p.4116-4119
Hauptverfasser: Han, Jeong-Seok, Lowary, Todd L
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Chemistry
Combinatorial Chemistry Techniques
Crystallography, X-Ray
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic Compounds, 3-Ring - analysis
Heterocyclic Compounds, 3-Ring - chemical synthesis
Molecular Structure
Organic chemistry
Oxidation-Reduction
Plants, Medicinal - chemistry
Preparations and properties
Scrophularia - chemistry
Stereoisomerism
Thymidine - chemistry
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Zusammenfassung:Syntheses of buergerinin F (1) and buergerinin G (2) were carried out to establish the absolute stereochemistry of these natural products. A linear sequence was used to synthesize 1 in 15 steps and 9% overall yield from thymidine. Subsequent oxidation of 1 with ruthenium tetroxide afforded 2 in 77% yield.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0341620