Synthetic studies on maitotoxin. 3. Stereoselective synthesis of the BCDE-ring system.
The stereoselective synthesis of the BCDE-ring system of maitotoxin has been accomplished through a two-directional strategy for the construction of polycyclic ether. The key reactions involve SmI 2-induced double cyclization of a beta-alkoxyacrylate and a double dihydroxylation for construction of the B- and E-rings.
Satoh
Masanori
M
Department of Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, Japan.
Koshino
Hiroyuki
H
Nakata
Tadashi
T
D000818:Animals; D003500:Cyclization; D004141:Dinoflagellida / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D035964:Oxocins / Q000138:chemical synthesis* / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000095702:Polyether Toxins
D004987:Ethers; D008387:Marine Toxins; D035964:Oxocins; D011083:Polycyclic Compounds; C020394:maitotoxin; D000095702:Polyether Toxins