Art

J-GLOBAL ID：201102212414591857   Reference number：11A0582418

EFFICIENT PHENOLIC OXIDATIONS TO CONSTRUCT ORTHO-SPIROLACTONE STRUCTURES USING OXO-BRIDGED HYPERVALENT IODINE(III) COMPOUND

オルソスピロラクトン構造を構築するためのオキソ架橋された超原子価ヨウ素(III)化合物を用いた効率的なフェノール酸化

Author (7)： TAKENAGA Naoko (Osaka Univ., Osaka, JPN) ,  UCHIYAMA Teruyoshi (Ritsumeikan Univ., Shiga, JPN) ,  KATO Daishi (Ritsumeikan Univ., Shiga, JPN) ,  FUJIOKA Hiromichi (Osaka Univ., Osaka, JPN) ,  DOHI Toshifumi (Osaka Univ., Osaka, JPN) ,  DOHI Toshifumi (Ritsumeikan Univ., Shiga, JPN) ,  KITA Yasuyuki (Ritsumeikan Univ., Shiga, JPN)
Material： Heterocycles  (International Journal for Reviews and Communications in Heterocyclic Chemistry)
Volume： 82  Issue： 2  Page： 1327-1336  Publication year： Mar. 01, 2011 
JST Material Number： S0966A  ISSN： 0385-5414  CODEN： HTCYAM  Document type： Article
Article type： 原著論文  Country of issue： Japan (JPN)  Language： ENGLISH (EN)

Thesaurus term： lactone ,  phenolic compound ,  oxidation ,  *spiro-compound ,  cyclization reaction ,  iodosyl compound

JST classification (1)： Furans  (CF07072V)

Substance index (2)： Iodosobenzene diacetate ,  PIFA

Reference (9)：

• Recent reviews and publications: a) P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123; b) Y. Kita, T. Takada, and H. Tohma, Pure Appl. Chem., 1996, 68, 627; c) A. Kirschning, Eur. J. Org. Chem., 1998, 2267; d) V. V. Zhdankin and P. J. Stang, Chem. Rev., 2002, 102, 2523; e) Hypervalent Iodine Chemistry; T. Wirth, Ed.; Springer-Verlag: Berlin, Heidelberg, 2003; f) H. Tohma and Y. Kita, Top Curr. Chem., 2003, 224, 209; g) V. V. Zhdankin and P. J. Stang, Chem. Rev., 2008, 108, 5299; h) T. Dohi and Y. Kita, Chem. Commun., 2009, 2073.
• Our previous works for phenolic oxidations: a) Y. Tamura, T. Yakura, J. Haruta, and Y. Kita, J. Org. Chem., 1987, 52, 3927; b) Y. Kita, H. Tohma, K. Kikuchi, M. Inagaki, and T. Yakura, J. Org. Chem., 1991, 56, 435; c) Y. Kita, H. Tohma, M. Inagaki, K. Hatanaka, and T. Yakura, J. Am. Chem. Soc., 1992, 114, 2175; d) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, and T. Takada, J. Org. Chem., 1998, 63, 6625; e) H. Tohma, Y. Harayama, M. Hashizume, M. Iwata, M. Egi, and Y. Kita, Angew. Chem., 2002, 114, 358; Angew. Chem. Int. Ed., 2002, 41, 348; f) T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, and Y. Kita, Angew. Chem. Int. Ed., 2005, 44, 6193; g) T. Dohi, Y. Minamitsuji, A. Maruyama, S. Hirose, and Y. Kita, Org. Lett., 2008, 10, 3559; h) Y. Minamitsuji, D. Kato, H. Fujioka, T. Dohi, and Y. Kita, Aust. J. Chem., 2009, 62, 648.
• a) T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, and Y. Kita, Angew. Chem. Int. Ed., 2008, 47, 3787; b) T. Dohi, Y. Kita, and A. Maruyama, Jpn. Kokai Tokkyo Koho, 2009149564A, 2009.
• For recent reports of natural product syntheses containing the ortho-spirolactone structures, see: a) C. Cox and S. J. Danishefsky, Org. Lett., 2000, 2, 3493; b) T. Siu, C. D. Cox, and S. J. Danishefsky, Angew. Chem., 2003, 115, 5787; Angew. Chem. Int. Ed., 2003, 42, 5629; c) D. A. Henderson, P. N. Collier, G. Pave, P. Rzepa, A. J. P. White, J. N. Burrows, and A. G. M. Barrett, J. Org. Chem., 2006, 71, 2434; d) F. Konno, T. Ishikawa, M. Kawahata, and K. Yamaguchi, J. Org. Chem., 2006, 71, 9818.
• For previous report on the structure of 4, see: J. Gallos, A. Varvoglis, and N. W. Alcock, J. Chem. Soc., Perkin Trans. 1, 1985, 757.

Terms in the title (4)： 構築 ,  架橋 ,  超原子価ヨウ素 ,  フェノール酸