Maitotoxin Extraction Maitotoxin Extraction [11 o5C年1m VK的络gg.na Structure Elucidation of Maitotoxin 梦罗 Degradation of maitoloxin (m 8*g the 特务 3 3 67 Maitotoxin Extraction Large-scale culture Were continued for Over ten years to yield around 10-20 mg of the pure sample From 4000 L of the Culture. 4000 L 村田 道雄 68 Maitotoxin Extraction 69 degradation reduction Structure Elucidation of Maitotoxin 70 Degradation of maitotoxin (Yasumoto, et al, 1992) [1] M. Murata, T. Iwashita, A. Yokoyama, M. Sasaki, T. Yasumoto, J. Am. Chem. Soc. 1992, 114, 6594. [2] a) M. Murata, H. Naoki, T. Iwashita, S. Matusunaga, M. Sasaki, A. Yokoyama, T. Yasumoto, J. Am. Chem. Soc. 1993, 115, 2060; b) M. Murata, H. Naoki, S. Matsunaga, M. Satake, T. Yasumoto, J. Am. Chem. Soc. 1994, 116, 7098; c) M. Satake, S. Ishida, T. Yasumoto, M. Murata, H. Utsumi, T. Hinomoto, J. Am. Chem. Soc. 1995, 117, 7019. 71 ? ? In 2006, the assigned structure of maitotoxin came under close scrutiny by Gallimore and Spencer on the basis of biosynthetic considerations, which suggested the opposite configuration at the two stereocenters of the JK junction (C-51, C-52). O O O O O O O O O O O O O OH O O O OH O O O O HO OH O OH S O O ONa HO OH OH OH OH OH O S O ONa HO OH O H H H H H H H HO H H H H H H H H OH OHH H H H H H OH H OH HO OH H H OH H H OH OH H H HO H H H H H O O O O O O O OH H H H H H H H H H HO H A B C D E F G H I J K L M N P Q R S T U V Y X W 51 52 O O O O O HO OH H H H H H H O Z A' B' D C' ' F E' ' 72