C-glycosides to fused polycyclic ethers. An efficient entry into the A-D ring system of gambierol.
[reaction: see text]. This Letter describes our use of C-glycosides to synthesize the A-D ring system of the marine ladder toxin gambierol in 20 steps.
Cox
J M
JM
Department of Chemistry, The University of Arizona, Tucson, 85721, USA.
Rainier
J D
JD
D000818:Animals; D002922:Ciguatoxins; D004141:Dinoflagellida / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D008386:Marine Biology; D008968:Molecular Conformation; D011083:Polycyclic Compounds / Q000737:chemistry*; D035964:Oxocins
D002922:Ciguatoxins; D004987:Ethers; D004988:Ethers, Cyclic; D006027:Glycosides; D011083:Polycyclic Compounds; C435770:gambierol; D035964:Oxocins