Synthetic studies on maitotoxin. 2. Stereoselective synthesis of the WXYZA'-ring system.
The stereoselective synthesis of the WXYZA'-ring system of maitotoxin has been accomplished via a linear synthetic approach, in which key reactions were SmI 2-induced cyclization of beta-alkoxyacrylate for the construction of the A'-, Y-, and X-rings and 6- endo cyclization of hydroxy vinylepoxide for that of the Z- and W-rings.
Morita
Masayuki
M
RIKEN, The Institute of Physical and Chemical Research, Saitama, Japan.
Haketa
Tasuku
T
Koshino
Hiroyuki
H
Nakata
Tadashi
T
D000818:Animals; D003500:Cyclization; D004141:Dinoflagellida / Q000737:chemistry; D004988:Ethers, Cyclic / 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
D004988:Ethers, Cyclic; D008387:Marine Toxins; D035964:Oxocins; D011083:Polycyclic Compounds; C020394:maitotoxin; D000095702:Polyether Toxins