Studies toward the total synthesis of gambieric acids: stereocontrolled synthesis of a DEFG-ring model compound.
A stereocontrolled convergent synthesis of a DEFG-ring model compound of gambieric acids, highly potent antifungal marine polycyclic ether natural products, has been achieved based on Suzuki-Miyaura coupling. Conformational analysis of the model compound revealed that the nine-membered F-ring exists exclusively as a single stable conformer, as opposed to that of ciguatoxins.
Fuwa
Haruhiko
H
Laboratory of Biostructural Chemistry, Graduate School of Life Sciences, Tohoku University, 2-1-1 Katahira, Aoba-ku, Sendai 980-8577, Japan. hfuwa@bios.tohoku.ac.jp
Noji
Sayaka
S
Sasaki
Makoto
M
D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D002922:Ciguatoxins