Chemical Synthesis of the GHIJKLMNO Ring System of Maitotoxin.
As the largest secondary metabolite to be discovered as of yet, the polyether marine neurotoxin maitotoxin constitutes a major structural and synthetic challenge. After its originally proposed structure ( 1) had been questioned on the basis of biosynthetic considerations, we provided computational and experimental support for structure 1. In an effort to provide stronger experimental evidence of the molecular architecture of maitotoxin, its GHIJKLMNO ring system 3 was synthesized. The (13)C NMR chemical shifts of synthetic 3 matched closely those corresponding to the same domain of the natural product providing strong evidence for the correctness of the originally proposed structure of maitotoxin ( 1).
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. kcn@scripps.edu
Frederick
Michael O
MO
Burtoloso
Antonio C B
AC
Denton
Ross M
RM
Rivas
Fatima
F
Cole
Kevin P
KP
Aversa
Robert J
RJ
Gibe
Romelo
R
Umezawa
Taiki
T
Suzuki
Takahiro
T
D002241:Carbohydrates / Q000737:chemistry; D002247:Carbon Isotopes; D005663:Furans / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis*; D019906:Nuclear Magnetic Resonance, Biomolecular; D035964:Oxocins / Q000138:chemical synthesis*; D000095702:Polyether Toxins
D002241:Carbohydrates; D002247:Carbon Isotopes; D005663:Furans; D008387:Marine Toxins; D035964:Oxocins; C020394:maitotoxin; D000095702:Polyether Toxins