Synthesis maitotoxin

Kishi Y, Synthesis of maitotoxin. Pure andAppl Chem 70 339—344, 1998. 

An impressively complex natural molecule is maitotoxin, a remarkable biologically active compound produced by the dinoflagellate Gambierdiscus toxicus. Presently, the total synthesis of this natural substance seems to be beyond the possibilities offered by modem synthesis. M. Sasaki, N. Matsumori, T. Maruyama, T. Nonomura, M. Murata, K. Tachibana, T. Yasumoto, Angew. Chem. Int. Ed. 1996, 35, 1672-1674. 

Sasaki, M, Nonomura, T, Murata, M, Tachibana, K, Synthesis and stereochemical confirmation of the cA-fused L/M and N/O ring systems of maitotoxin. Tetrahedron Lett., 35, 5023-5026, 1994. 

G. to V j that produces ciguatoxin precursors (142—147) and maitotoxin (148). The absolute stereochemistry of gambieric acids A-D (149-152) were assigned by the modified Mosher s method, conformational analysis based on J values and NOE correlations, chiral fluorimetric HPLC analysis, and synthesis of A/B-ring models of gambieric acids A-D (149-152). ... 

Complex polyether marine natural product toxins continue to attract synthetic attention, and this year has again seen several interesting papers in this area. The complete relative stereochemistry of maitotoxin has finally been resolved with the publication of a major paper by Kishi s group on the synthesis of various fragments of the natural product. o-Ribose was converted to 196, containing the C10-C15 component (this synthesis utilized diastereoselective indium-mediated... 

Maitotoxin is one of the most conqilex (32 ether rings) marine polyedio natural Hoduct toxins so far discovered, and one of the most potmt toxins known. D-Glucose has been converted to 138 conrirming the stereochemistry of the L/M and N/0 ring systrans of maitotoxin. The synthesis... 

Nakata, T., Nomura, S., and Matsukura, H. (1996) Stereoselective synthesis of the S- and Y-ring systems of maitotoxin. Chem. Pharm. Butt., 44, 627-629. 

Satoh, M., Mori, M., and Nakata, T. (2007) Stereoselective synthesis of the GHI-ring of maitotoxin, a marine polycyclic ether. Heterocycles, 74,259-263. 

Morita, M Haketa, T., Koshino, H and Nakata, T. (2008) Synthetic studies on maitotoxin. 2. Stereoselective synthesis of the WXYZA -ring system. Org. Lett., 10,1679-1682. 

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