Total synthesis of gambierol.
The convergent total synthesis of gambierol (1) is described. The octacyclic ether framework of 1 was constructed via the intramolecular allylation of alpha-chloroacetoxy ether followed by ring-closing metathesis. A modified Stille coupling was successfully applied to the synthesis of the triene side chain.
Kadota
Isao
I
Research Center for Sustainable Materials Engineering, Institute of Multidisciplinary Research for Advanced Materials, and Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Takamura
Hiroyoshi
H
Sato
Kumi
K
Ohno
Akio
A
Matsuda
Kumiko
K
Yamamoto
Yoshinori
Y
D000818:Animals; D002922:Ciguatoxins; D004141:Dinoflagellida / Q000737:chemistry; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D008387:Marine Toxins / Q000138:chemical synthesis*; D009498:Neurotoxins / Q000138:chemical synthesis; D011083:Polycyclic Compounds / Q000138:chemical synthesis*; D035964:Oxocins
D002922:Ciguatoxins; D004988:Ethers, Cyclic; D008387:Marine Toxins; D009498:Neurotoxins; D011083:Polycyclic Compounds; C435770:gambierol; D035964:Oxocins