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J-GLOBAL ID：201402209318294516   Reference number：14A0191348

SYNTHETIC STUDIES OF YESSOTOXIN: ITERATIVE SYNTHESIS OF THE AB RING SYSTEM VIA PD(II)-CATALYZED CYCLIZATION OF ALCOHOL

イエッソトキシンの合成研究: Pd(II)触媒を使ったアルコールの環化反応によるAB環構造の反復合成

Author (5)： YOKOYAMA Hajime (Univ. Toyama, Toyama, JPN) ,  KUSUMOTO Yasuhiro (Univ. Toyama, Toyama, JPN) ,  SUMIYOSHI Koshiro (Univ. Toyama, Toyama, JPN) ,  MIYAZAWA Masahiro (Univ. Toyama, Toyama, JPN) ,  HIRAI Yoshiro (Univ. Toyama, Toyama, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 89  Issue： 2  Page： 353-358  Publication year： Feb. 01, 2014 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 短報  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： *oxygen heterocyclic compound ,  palladium catalyst ,  *catalytic reaction ,  chemical synthesis ,  molecular structure ,  ring structure ,  *cyclization reaction ,  *aliphatic alcohol
Semi thesaurus term： ring structure

JST classification (4)： Oxygen heterocycles in general  (CF07020K) ,  Catalytic reactions in general  (CB06080F) ,  Cyclization reaction,ring-opening reaction  (CF02050I) ,  Aliphatic alcohols  (CF03090H)

Substance index (1)： Yessotoxin

Reference (8)：

• (a) M. Murata, M. Kumagai, J. S. Lee, and T. Yasumoto, Tetrahedron Lett., 1987, 28, 5869; (b) M. Satake, K. Terasawa, Y. Kadowaki, and T. Yasumoto, Tetrahedron Lett., 1996, 37, 5955; (c) H. Takahashi, T. Kusumi, Y. Kan, M. Satake, and T. Yasumoto, Tetrahedron Lett., 1996, 37, 7087.
• Synthetic studies of yessotoxin and its analogs, see: (a) Y. Mori and H. Hayashi, Tetrahedron, 2002, 58, 1789; (b) K. Suzuki and T. Nakata, Org. Lett., 2002, 4, 3943; (c) Y. Mori, K. Nogami, H. Hayashi, and R. Noyori, J. Org. Chem., 2003, 68, 9050; (d) Y. Mori, T. Takase, and R. Noyori, Tetrahedron Lett., 2003, 44, 2319; (e) T. Oishi, K. Watanabe, and M. Murata, Tetrahedron Lett., 2003, 44, 7315; (f) I. Kadota, H. Ueno, and Y. Yamamoto, Tetrahedron Lett., 2003, 44, 8935; (g) K. Watanabe, M. Suzuki, M. Murata, and T. Oishi, Tetrahedron Lett., 2005, 46, 3991; (h) I. Kadota, H. Ueno, Y. Sato, and Y. Yamamoto, Tetrahedron Lett., 2006, 47, 89; (i) T. Oishi, M. Suzuki, K. Watanabe, and M. Murata, Tetrahedron Lett., 2006, 47, 3975; (j) I. Kadota, T. Abe, Y. Sato, C. Kabuto, and Y. Yamamoto, Tetrahedron Lett., 2006, 47, 6545; (k) K. Torikai, K. Watanabe, H. Minato, T. Imaizumi, M. Murata, and T. Oishi, Synlett, 2008, 2368; (l) T. Oishi, T. Imaizumi, and M. Murata, Chem. Lett., 2010, 39, 108; (m) T. Sakai, A. Sugimoto, H. Tatematsu, and Y. Mori, J. Org. Chem., 2012, 77, 11177.
• (a) H. Yokoyama, S. Nakayama, M. Murase, M. Miyazawa, S. Yamaguchi, and Y. Hirai,Heterocycles, 2009, 77, 211; (b) H. Yokoyama and Y. Hirai, Heterocycles, 2008, 75, 2133; (c) H. Yokoyama, H. Kobayashi, M. Miyazawa, S. Yamaguchi, and Y. Hirai, Hetreocycles, 2007, 74, 283; (d) H. Yokoyama, H. Ejiri, M. Miyazawa, S. Yamaguchi, and Y. Hirai, Tetrahedron: Asymmetry, 2007, 18, 852; (e) M. Miyazawa, M. Narantsetseg, H. Yokoyama, S. Yamaguchi, and Y. Hirai, Heterocycles, 2004, 63, 1017; (f) H. Yokoyama, K. Otaya, H. Kobayashi, M. Miyazawa, S. Yamaguchi, and Y. Hirai, Org. Lett., 2000, 2, 2427; (g) Y. Hirai, J. Watanabe, T. Nozaki, H. Yokoyama, and S. Yamaguchi, J. Org. Chem., 1997, 62, 776.
• H. Yokoyama, Y. Hayashi, Y. Nagasawa, H. Ejiri, M. Miyazawa, and Y. Hirai, Tetrahedron, 2010, 66, 8458.
• Absolute configuration of the triol (2) was assigned tentatively by application of the Sharpless mnemonic. See: S. Alvarez, R. Alvarez, and A. R. deLera, Tetrahedron: Asymmetry, 2004, 15, 839. The enantiomeric ratio of the triol (2) was determined by ¹H NMR analysis of Ο-methylmandelate ester derivatives of 2.

Terms in the title (8)： イエッソトキシン ,  研究 ,  PD ,  触媒 ,  アルコール ,  環化反応 ,  環構造 ,  反復