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BIBTEX RIS

Synthesis of vitamin D 3 and related compounds

1987; Wiley; Volume: 7; Issue: 2 Linguagem: Inglês

10.1002/med.2610070202

ISSN

1098-1128

Autores

Tetsuji Kametani, H. FURUYAMA,

Tópico(s)

Synthesis and Reactivity of Heterocycles

Resumo

Medicinal Research ReviewsVolume 7, Issue 2 p. 147-171 Article Synthesis of vitamin D3 and related compounds Tetsuji Kametani, Tetsuji Kametani Institute of Medicinal Chemistry, Hoshi University, Ebara 2–4–41 Shinagawa-ku, Tokyo 142, JapanSearch for more papers by this authorHiroko Furuyama, Hiroko Furuyama Institute of Medicinal Chemistry, Hoshi University, Ebara 2–4–41 Shinagawa-ku, Tokyo 142, JapanSearch for more papers by this author Tetsuji Kametani, Tetsuji Kametani Institute of Medicinal Chemistry, Hoshi University, Ebara 2–4–41 Shinagawa-ku, Tokyo 142, JapanSearch for more papers by this authorHiroko Furuyama, Hiroko Furuyama Institute of Medicinal Chemistry, Hoshi University, Ebara 2–4–41 Shinagawa-ku, Tokyo 142, JapanSearch for more papers by this author First published: April/June 1987 https://doi.org/10.1002/med.2610070202Citations: 52AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Reference 1(a) N. Ikekawa and T. Takeshita, Yuki Gosei Kagaku Kyokai Shi, 37, 755 (1979); (b) N. Ikekawa, Kagaku To Seibutsu, 16, 287 (1978); (c) C. Kaneko, Yuki Gosei Kagaku Kyokai Shi, 33, 75 (1975); (d) P. E. Georghiou, Chem. Soc. Rev., 1977, 83. 2 N. Ikekawa, Gekkan Yakuji, 26, 43 (1984). 3 S. Yamada, K. Yamamoto, H. Naito, T. Suzuki, M. Ohmori, H. Takayama, Y. Shiina, C. Miyaura, H. Tanaka, E. Abe, T. Suda, I. Matsunaga, and Y. Nishii, J. Med. Chem., 22, 1148 (1985). 4 Y. Kobayashi and T. Taguchi, Yuki Gosei Kagaku Kyokai Shi, 43, 1073 (1985). 5 A. Windaus, M. Deppe, and W. W. Wunderlick, Ann., 533, 118 (1938). 6 D. H. R. Barton, R. H. Hesse, M. M. Pechet, and E. Rizzardo, J. Am. Chem. Soc., 95, 2748 (1973); (b) J. Chem. Soc., Chem. Commun., 1974, 203. 7 A. Rotman and Y. Mazur, J. Chem. Soc., Chem., Commun., 1974, 15; E. Keinan and Y. Mazur, J. Org. Chem., 43, 1020 (1978). 8 Z. Cohen, E. Keinan, Y. Mazur, and A. Ulman, J. Org. Chem., 41, 2651 (1976). 9 M. L. Mihailovic, L. Lorenc, and V. Pavlovic, Tetrahedron, 33, 441 (1977). 10 A. Emke, D. Hands, H. M. Midgley, W. B. Whalley, and R. Ahmad, J. Chem. Soc., Perkin Trans. 1, 1977, 820. 11 L. Vanmaele, P. J. De Clercq, and M. Vandewalle, Tetrahedron Lett., 41, 141 (1985). 12 S. K. Dasgupta, K. R. Crump, and M. Gut, J., Org. Chem., 39, 1658 (1974). 13 M. Morisaki, J. Rubio-Lightbourn, N. Ikekawa, and T. Takeshita, Chem. Pharm. Bull., 21, 457 (1973). 14 W. G. Salmond, M. C. Sobala, and K. D. Maisto, Tetrahedrom Lett., 1977, 1237. 15 W. G. Salmond and M. C. Sobala, Tetrahedron Lett., 1977, 1695. 16 W. G. Salmond, M. A. Barta, and J. L. Havens, J. Org. Chem., 43, 790 (1978). 17 A. Fürst, L. Labler, and W. Meier, Helv. Chim. Acta, 65, 1499 (1982). 18 S. C. Eyley and D. H. Williams, J. Chem. Soc., Perkin Trans. 1, 1976, 731. 19 N. Ikekawa, M. Morisaki, H. Ohtaka, and Y. Chiyoga, J. Chem. Soc., Chem. Commun., 1971, 1498; H. Ohtaka, M. Morisaki, and N. Ikekawa, J. Org. Chem., 38, 1688 (1973). 20 T. Takeshita, S. Ishimoto, and N. Ikekawa, Chem. Pharm. Bull., 24, 1931 (1976). 21 M. Morisaki, J. Rubio-Lightbourn, N. Ikekawa, and T. Takeshita, Chem. Pharm. Bull., 21, 2568 (1973). 22 T. A. Narwid, K. E. Cooney, and M. R. Uskoković, Helv. Chim. Acta, 57, 771 (1974). 23 J. Wicha and K. Bai, J. Chem. Soc., Chem. Commun., 1975, 968. 24 B. M. Trost and T. R. Verhoeven, J. Am. Chem. Soc., 100, 3435 (1978); B. M. Trost and Y. Matsumura, J. Org. Chem., 42, 2036 (1977); J. S. Temple and J. Schwartz, J. Am. Chem. Soc., 102, 7381 (1980); M. Reidiker and J. Schwartz, Tetrahedron Lett., 22, 4655 (1981). 25 J. P. Marino and H. Abe, J. Am. Chem. Soc., 103, 2907 (1981). 26 M. Koreeda, Y. Tanaka, and A. Schwartz, J. Org. Chem., 45, 1172 (1980); M. Tanabe and K. Hayashi, J. Am. Chem. Soc., 102, 862 (1980). 27(a) W. G. Dauben and T. Brookhart, J. Am. Chem. Soc., 103, 237 (1981); (b) A. D. Batcho, D. E. Berger, and M. R. Uskoković, J. Am. Chem Soc., 103, 1293 (1981); (c) A. D. Batcho, D. E. Berger, S. G. Dauvoust, P. M. Wovkulich, and M. R. Uskoković, Helv. Chim. Acta, 64, 1682 (1981). 28 M. M. Midland and Y. C. Kwon, Tetrahedron Lett., 23, 2077 (1982). 29(a) K. Ochi, I. Matsunaga, M. Shindo, and C. Kaneko, Steroids, 30, 795 (1977); (b) J. Chem. Soc., Perkin Trans. 1, 1979, 161; (c) K. Ochi, I. Matsunaga, H. Nagano, M. Fukushima, M. Shindo, C. Kaneko, M. Ishikawa, and H. F. DeLuca, J. Chem. Soc., Perkin Trans. 1, 1979, 165. 30 W. G. Salmond, Fourth Workshop on Vitamin D, Berlin, Feb. 1979, Abstracts, p. 5. 31 M. Sheves and Y. Mazur, J. Am. Chem. Soc., 97, 6249 (1975). 32 H. H. Inhoffen, K. Irmscher, H. Hirschfeld, U. Stache, and A. Kreuzer, Chem. Ber., 91, 2309 (1958). 33 I. T. Harrison and B. Lythgoe, J. Chem. Soc., 1958, 837. 34 A. Windaus and U. Riemann, Z. Physiol. Chem., 274, 206 (1942). 35 T. M. Dawson, J. Dixon, P. S. Littlewood, B. Lythgoe, and A. K. Saksena, J. Chem. Soc. (C), 1971, 2960. 36 P. S. Littlewood, B. Lythgoe, and A. K. Saksena, J. Chem. Soc. (C), 1971, 2955. 37 T. M. Dawson, J. Dixon, P. S. Littlewood, and B. Lythgoe, J. Chem. Soc. (C), 1971, 2352. 38 B. Lythgoe, T. A. Moran, M. E. N. Nambudiry, J. Tideswell, and P. W. Wright, J. Chem. Soc., Perkin Trans. 1, 1978, 590. 39 H. H. Inhoffen, G. Quinkert, S. Schütz, D. Kampe, and G. F. Domagk, Chem. Berg., 90, 664 (1957). 40 H. Nemoto, K. Suzuki, M. Tsubuki, K. Minemura, K. Fukumoto, H. Furuyama, and T. Kametani, Tetrahedron, 39, 1123 (1983). 41 T. Kametani, M. Kajiwara, and K. Fukumoto, Tetrahedron, 30, 1053 (1974). 42 J. W. J. Gielen, R. B. Koolstra, H. J. C. Jacobs, and E. Havinga, Recl. Trav. Chim. Pays-Bas, 99, 306 (1980). 43 H. Nemoto, X.-M. Wu, H. Kurobe, M. Ihara, K. Fukumoto, and T. Kametani, Tetrahedron Lett., 24, 4257 (1983); H. Nemoto, X.-M. Wu, H. Kurobe, K. Fukumoto, and T. Kametani, Tetrahedron Lett., 25, 3095 (1984). 44(a) H. E. Paaren, H. F. DeLuca, and H. K. Schnoes, J. Org. Chem., 45, 3253 (1980); (b) M. Sheves and Y. Mazur, J. Am. Chem. Soc., 97, 6249 (1975). 45 P. R. Story, J. A. Alford, J. R. Burgess, and W. C. Ray, J. Am. Chem. Soc., 93, 3042 (1971). 46 D. R. Williams, K. Nishitani, W. Bennett, and S. Y. Sit, Tetrahedron Lett., 22, 3745 (1981). 47 H. Nemoto, H. Kurobe, K. Fukumoto, and T. Kametani, Chem. Lett., 1985, 259; Heterocycles, 23, 567 (1985). 48 P. J. Kocienski, B. Lythgoe, and S. Ruston, J. Chem. Soc., Perkin Trans. 1, 1979, 1290. 49 M. Julia and J.-M. Paris, Tetrahedron Lett., 1973, 4833. 50 Z. G. Hajos and D. R. Parrish, J. Org. Chem., 39, 1615 (1974). 51 H. T. Toh and W. H. Okamura, J. Org. Chem., 48, 1414 (1983). 52(a) B. Lythgoe, D. A. Roberts, and I. Waterhouse, J. Chem. Soc., Perkin Trans. 1, 1977, 2608; (b) C. B. Chapleo, P. Hallett, B. Lythgoe, I. Waterhouse, and P. W. Wright, J. Chem. Soc., Perkin. Trans 1, 1977, 1211. 53 M. Tamura and J. Kochi, Synthesis, 1971, 303. 54 H. C. Brown and P. Geoghegan, J. Am. Chem. Soc., 89, 1522 (1967). 55 E. G. Baggiolini, J. A. Lacobelli, B. M. Hennessy, and M. R. Uskoković, J. Am. Chem. Soc., 104, 2945 (1982). 56(a) B. Lythgoe, Chem. Soc. Rev., 1980, 449; P. J. Kocienski and B. Lythgoe, J. Chem. Soc., Perkin Trans. 1, 1980, 1400; (b) P. J. Kocienski, B. Lythgoe, and I. Waterhouse, Tetrahedron Lett., 1979, 4419; R. G. Harrison, B. Lythgoe, and P. W. Wright, J. Chem. Soc., Perkin Trans. 1, 1974, 2654; (c) R. G. Harrison, B. Lythgoe, and P. W. Wright, Tetrahedron Lett., 1973, 3649 (d) B. Lythgoe, M. E. N. Nambudiry, and J. Tideswell, Tetrahedron Lett., 1977, 3685. 57 R. A. Micheli, Z. G. Hajos, N. Cohen, D. R. Parrish, L. A. Portland, W. Sciamanna, M. A. Scott, and P. A. Wehrli, J. Org. Chem., 38, 3239 (1973). 58 H. Nemoto, T. Kimura, H. Kurobe, K. Fukumoto, and T. Kametani, J. Chem. Soc., Perkin Trans. 1, 1986, 1777. 59 B. M. Trost, P. R. Bernstein, and P. C. Funfschilling, J. Am. Chem. Soc., 101, 4378 (1979). 60 W. S. Johnson, J. D. Elliott, and G. J. Hanson, J. Am. Chem. Soc., 106, 1138 (1984). 61 S. Hatakeyama, H. Numata, and S. Takano, Tetrahedron Lett., 25, 3617 (1984). 62 R. V. Stevens and D. S. Lawrence, Tetrahedron, 41, 93 (1985). 63 Y. Kobayashi, T. Taguchi, T. Terada, J. Oshida, M. Morisaki, and N. Ikekawa, Tetrahedron Lett., 22, 2023 (1979); S. Yamada, M. Ohmori, and H. Takayama, Tetrahedron Lett., 1979, 1859. 64 A. B. Parsippany, J. J. Patridge, and M. R. Uskoković, U. S. Patent, 4,397,847 (1983). 65 E. Ohshima, H. Sai, S. Takatsuto, N. Ikekawa, Y. Kobayashi, Y. Tanaka, and H. F. DeLuca, Chem. Pharm. Bull., 32, 3525 (1984). 66 T. Taguchi, S. Mitsuhashi, A. Yamanouchi, Y. Kobayahi, H. Sai, and N. Ikekawa, Tetrahedron Lett., 25, 4933 (1984). 67 H. F. DeLuca, Y. Tanaka, N. Ikekawa, and Y. Kobayashi, U. S. Patent, 4,500,460; 4,502,991 (1985). 68 Y. Kobayashi, T. Taguchi, N. Kanuma, N. Ikekawa, and J. Oshida, J. Chem. Soc., Chem. Commun., 1980, 459. 69 Y. Kobayashi, T. Taguchi, S. Mitsuhashi, T. Eguchi, E. Ohshima, and N. Ikekawa, Chem. Pharm. Bull., 30, 4297 (1982). 70 Y. Kobayashi, T. Taguchi, and N. Kanuma, Tetrahedron Lett., 22, 4309 (1981). 71 J. Oshida, M. Morisaki, and N. Ikekawa, Tetrahedron Lett., 21, 1755 (1980). 72 W. G. Dauben, B. Kohler, and A. Roesle, J. Org. Chem., 50, 2007 (1985). 73 K. Nakayama, S. Yamada, H. Takayama, Y. Nawata, and Y. Iitaka, J. Org. Chem., 49, 1537 (1984). 74 S. Jeganathan, A. D. Johnson, E. A. Kuenzel, A. W. Norman, and W. H. Okamura, J. Org. Chem., 49, 2152 (1984). 75 S. Yamada, K. Yamamoto, H. Naito, T. Suzuki, M. Ohmori, H. Takayama, Y. Shiina, C. Miyaura, H. Tanaka, E. Abe, T. Suda, I. Matsunaga, and Y. Nishii, J. Med. Chem., 28, 1148 (1985); J. Med. Chem., 28, 1153 (1985). 76 H. Sai, S. Takatsuto, N. Hara, and N. Ikekawa, Chem. Pharm. Bull., 33, 878 (1985). 77 H. Sai, S. Takatsuto, and N. Ikekawa, Chem. Pharm. Bull., 33, 4815 (1985). 78 H. T. Toh and W. H. Okamura, J. Org. Chem., 48, 1414 (1983). Citing Literature Volume7, Issue2April/June 1987Pages 147-171 ReferencesRelatedInformation

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