Stereoselective syntheses of the C'D'E'F'-ring system of maitotoxin and the FG-ring system of gambierol.
[structure: see text]. The stereoselective syntheses of the C'D'E'F'-ring system of maitotoxin and the FG-ring system of gambierol were accomplished. The key steps involve 6-endo-cyclization of methylepoxide, SmI2-induced reductive cyclization, 6-endo-cyclization of vinylepoxide, and formation of the lactone ring.
Sakamoto
Y
Y
RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan.
Matsuo
G
G
Matsukura
H
H
Nakata
T
T
D002922:Ciguatoxins; D004988:Ethers, Cyclic / Q000737:chemistry*; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D035964:Oxocins; D011083:Polycyclic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D000095702:Polyether Toxins
D002922:Ciguatoxins; D004988:Ethers, Cyclic; D008387:Marine Toxins; D035964:Oxocins; D011083:Polycyclic Compounds; C435770:gambierol; C020394:maitotoxin; D000095702:Polyether Toxins