Stereochemistry, Total Synthesis, and Biological Evaluation of the New Plant Hormone Solanacol

Stereochemistry, Total Synthesis, and Biological Evaluation of the New Plant Hormone Solanacol

The first total synthesis of solanacol, a member of the strigolactone family, features ring‐closing metathesis, enzymatic kinetic resolution, and atom‐transfer radical cyclization. This defines the stereostructure of the natural product. The best hormonal activity is revealed by an acetylated deriva...

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Veröffentlicht in:Chemistry : a European journal 2010-12, Vol.16 (47), p.13941-13945
Hauptverfasser: Chen, Victor X., Boyer, François-Didier, Rameau, Catherine, Retailleau, Pascal, Vors, Jean-Pierre, Beau, Jean-Marie
Format: Artikel
Sprache:eng
Schlagworte:
Biological Evolution
Chemical Sciences
Chemistry
Crystallography, X-Ray
hormones
kinetic resolution
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Organic chemistry
Plant Growth Regulators - chemical synthesis
Plant Growth Regulators - chemistry
radical reactions
Stereoisomerism
strigolactones
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Zusammenfassung:The first total synthesis of solanacol, a member of the strigolactone family, features ring‐closing metathesis, enzymatic kinetic resolution, and atom‐transfer radical cyclization. This defines the stereostructure of the natural product. The best hormonal activity is revealed by an acetylated derivative at O4 (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201002817