Synthesis and Structure Revision of Calyxin Natural Products

Synthesis and Structure Revision of Calyxin Natural Products

Tandem Prins cyclization and Friedel−Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, w...

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Veröffentlicht in:Journal of organic chemistry 2006-04, Vol.71 (8), p.3176-3183
Hauptverfasser: Tian, Xia, Jaber, James J, Rychnovsky, Scott D
Format: Artikel
Sprache:eng
Schlagworte:
Alpinia - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Chemistry
Cyclization
Exact sciences and technology
Molecular Structure
Morpholines - chemical synthesis
Morpholines - chemistry
Organic chemistry
Oxidation-Reduction
Seeds - chemistry
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Zusammenfassung:Tandem Prins cyclization and Friedel−Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060094g