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, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.
Tian
Xia
X
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, Irvine, California 92697, USA.
Jaber
James J
JJ
Rychnovsky
Scott D
SD
D032429:Alpinia / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D009025:Morpholines / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D012639:Seeds / Q000737:chemistry
D001688:Biological Products; D009025:Morpholines; C015554:tridemorph