Total synthesis of acanthacerebroside A and astrocerebroside A via a chiral epoxide intermediate derived from L-quebrachitol

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 1, 1998, Pages 259-272

  Chida, Noritaka ^a   Sakata, Noboru ^a   Murai, Katsuyuki ^a   Tobe, Takahiko ^a   Nagase, Toshihiko ^a   Ogawa, Seiichiro ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACANTHACEREBROSIDE A; ASTROCEREBROSIDE A; CEREBROSIDE; QUEBRACHITOL; UNCLASSIFIED DRUG;

ARTICLE; ASTERIAS; CHIRALITY; DRUG ISOLATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0031930827     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.259     Document Type: Article

References (72)

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6. a) Y. Kuwano, R. Higuchi, R. Isobe, and T. Komori, Liebigs Ann. Chem., 1988, 19;
7. b) R. Higuchi, M. Kagoshima, and T. Komori, Liebigs Ann. Chem., 1990, 659;
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11. d) S. Hirsch and Y. Kashman, Tetrahedron, 45, 3897 (1989); Y. Kawano, R. Higuchi, and T. Komori, Liebigs Ann. Chem., 1990, 43; R. Higuchi, K. Inukai, J. X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y. Nagai, Liebigs Ann. Chem., 1993, 359; R. Ishida, H. Shirahama, and T. Matsumoto, Chem. Lett., 1993, 9; T. Natori, Y. Koezuka, and T. Higa, Tetrahedron Lett., 34, 5591 (1993); T. Natori, M. Morita, K. Akimoto, and Y. Koezuka, Tetrahedron, 50, 2771 (1994); H.-y. Li, S. Matsunaga, and N. Fusetani, Tetrahedron, 51, 2273 (1995); V. Costantino, E. Fattorusso, and A. Mangoni, Liebigs Ann. Chem., 1995, 2133; R. Higuchi, S. Matsumoto, M. Fujita, and T. Komori, Liebigs Ann. Chem., 1995, 545; R. Higuchi, Y. Hurano, M. Mitsuyuki, R. Isobe, K. Yamada, T. Miyamoto, and T. Komori, Liebigs Ann. Chem., 1996, 593.
12. d) S. Hirsch and Y. Kashman, Tetrahedron, 45, 3897 (1989); Y. Kawano, R. Higuchi, and T. Komori, Liebigs Ann. Chem., 1990, 43; R. Higuchi, K. Inukai, J. X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y. Nagai, Liebigs Ann. Chem., 1993, 359; R. Ishida, H. Shirahama, and T. Matsumoto, Chem. Lett., 1993, 9; T. Natori, Y. Koezuka, and T. Higa, Tetrahedron Lett., 34, 5591 (1993); T. Natori, M. Morita, K. Akimoto, and Y. Koezuka, Tetrahedron, 50, 2771 (1994); H.-y. Li, S. Matsunaga, and N. Fusetani, Tetrahedron, 51, 2273 (1995); V. Costantino, E. Fattorusso, and A. Mangoni, Liebigs Ann. Chem., 1995, 2133; R. Higuchi, S. Matsumoto, M. Fujita, and T. Komori, Liebigs Ann. Chem., 1995, 545; R. Higuchi, Y. Hurano, M. Mitsuyuki, R. Isobe, K. Yamada, T. Miyamoto, and T. Komori, Liebigs Ann. Chem., 1996, 593.
13. d) S. Hirsch and Y. Kashman, Tetrahedron, 45, 3897 (1989); Y. Kawano, R. Higuchi, and T. Komori, Liebigs Ann. Chem., 1990, 43; R. Higuchi, K. Inukai, J. X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y. Nagai, Liebigs Ann. Chem., 1993, 359; R. Ishida, H. Shirahama, and T. Matsumoto, Chem. Lett., 1993, 9; T. Natori, Y. Koezuka, and T. Higa, Tetrahedron Lett., 34, 5591 (1993); T. Natori, M. Morita, K. Akimoto, and Y. Koezuka, Tetrahedron, 50, 2771 (1994); H.-y. Li, S. Matsunaga, and N. Fusetani, Tetrahedron, 51, 2273 (1995); V. Costantino, E. Fattorusso, and A. Mangoni, Liebigs Ann. Chem., 1995, 2133; R. Higuchi, S. Matsumoto, M. Fujita, and T. Komori, Liebigs Ann. Chem., 1995, 545; R. Higuchi, Y. Hurano, M. Mitsuyuki, R. Isobe, K. Yamada, T. Miyamoto, and T. Komori, Liebigs Ann. Chem., 1996, 593.
14. d) S. Hirsch and Y. Kashman, Tetrahedron, 45, 3897 (1989); Y. Kawano, R. Higuchi, and T. Komori, Liebigs Ann. Chem., 1990, 43; R. Higuchi, K. Inukai, J. X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y. Nagai, Liebigs Ann. Chem., 1993, 359; R. Ishida, H. Shirahama, and T. Matsumoto, Chem. Lett., 1993, 9; T. Natori, Y. Koezuka, and T. Higa, Tetrahedron Lett., 34, 5591 (1993); T. Natori, M. Morita, K. Akimoto, and Y. Koezuka, Tetrahedron, 50, 2771 (1994); H.-y. Li, S. Matsunaga, and N. Fusetani, Tetrahedron, 51, 2273 (1995); V. Costantino, E. Fattorusso, and A. Mangoni, Liebigs Ann. Chem., 1995, 2133; R. Higuchi, S. Matsumoto, M. Fujita, and T. Komori, Liebigs Ann. Chem., 1995, 545; R. Higuchi, Y. Hurano, M. Mitsuyuki, R. Isobe, K. Yamada, T. Miyamoto, and T. Komori, Liebigs Ann. Chem., 1996, 593.
15. d) S. Hirsch and Y. Kashman, Tetrahedron, 45, 3897 (1989); Y. Kawano, R. Higuchi, and T. Komori, Liebigs Ann. Chem., 1990, 43; R. Higuchi, K. Inukai, J. X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y. Nagai, Liebigs Ann. Chem., 1993, 359; R. Ishida, H. Shirahama, and T. Matsumoto, Chem. Lett., 1993, 9; T. Natori, Y. Koezuka, and T. Higa, Tetrahedron Lett., 34, 5591 (1993); T. Natori, M. Morita, K. Akimoto, and Y. Koezuka, Tetrahedron, 50, 2771 (1994); H.-y. Li, S. Matsunaga, and N. Fusetani, Tetrahedron, 51, 2273 (1995); V. Costantino, E. Fattorusso, and A. Mangoni, Liebigs Ann. Chem., 1995, 2133; R. Higuchi, S. Matsumoto, M. Fujita, and T. Komori, Liebigs Ann. Chem., 1995, 545; R. Higuchi, Y. Hurano, M. Mitsuyuki, R. Isobe, K. Yamada, T. Miyamoto, and T. Komori, Liebigs Ann. Chem., 1996, 593.
16. d) S. Hirsch and Y. Kashman, Tetrahedron, 45, 3897 (1989); Y. Kawano, R. Higuchi, and T. Komori, Liebigs Ann. Chem., 1990, 43; R. Higuchi, K. Inukai, J. X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y. Nagai, Liebigs Ann. Chem., 1993, 359; R. Ishida, H. Shirahama, and T. Matsumoto, Chem. Lett., 1993, 9; T. Natori, Y. Koezuka, and T. Higa, Tetrahedron Lett., 34, 5591 (1993); T. Natori, M. Morita, K. Akimoto, and Y. Koezuka, Tetrahedron, 50, 2771 (1994); H.-y. Li, S. Matsunaga, and N. Fusetani, Tetrahedron, 51, 2273 (1995); V. Costantino, E. Fattorusso, and A. Mangoni, Liebigs Ann. Chem., 1995, 2133; R. Higuchi, S. Matsumoto, M. Fujita, and T. Komori, Liebigs Ann. Chem., 1995, 545; R. Higuchi, Y. Hurano, M. Mitsuyuki, R. Isobe, K. Yamada, T. Miyamoto, and T. Komori, Liebigs Ann. Chem., 1996, 593.
17. d) S. Hirsch and Y. Kashman, Tetrahedron, 45, 3897 (1989); Y. Kawano, R. Higuchi, and T. Komori, Liebigs Ann. Chem., 1990, 43; R. Higuchi, K. Inukai, J. X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y. Nagai, Liebigs Ann. Chem., 1993, 359; R. Ishida, H. Shirahama, and T. Matsumoto, Chem. Lett., 1993, 9; T. Natori, Y. Koezuka, and T. Higa, Tetrahedron Lett., 34, 5591 (1993); T. Natori, M. Morita, K. Akimoto, and Y. Koezuka, Tetrahedron, 50, 2771 (1994); H.-y. Li, S. Matsunaga, and N. Fusetani, Tetrahedron, 51, 2273 (1995); V. Costantino, E. Fattorusso, and A. Mangoni, Liebigs Ann. Chem., 1995, 2133; R. Higuchi, S. Matsumoto, M. Fujita, and T. Komori, Liebigs Ann. Chem., 1995, 545; R. Higuchi, Y. Hurano, M. Mitsuyuki, R. Isobe, K. Yamada, T. Miyamoto, and T. Komori, Liebigs Ann. Chem., 1996, 593.
18. d) S. Hirsch and Y. Kashman, Tetrahedron, 45, 3897 (1989); Y. Kawano, R. Higuchi, and T. Komori, Liebigs Ann. Chem., 1990, 43; R. Higuchi, K. Inukai, J. X. Jhou, M. Honda, T. Komori, S. Tsuji, and Y. Nagai, Liebigs Ann. Chem., 1993, 359; R. Ishida, H. Shirahama, and T. Matsumoto, Chem. Lett., 1993, 9; T. Natori, Y. Koezuka, and T. Higa, Tetrahedron Lett., 34, 5591 (1993); T. Natori, M. Morita, K. Akimoto, and Y. Koezuka, Tetrahedron, 50, 2771 (1994); H.-y. Li, S. Matsunaga, and N. Fusetani, Tetrahedron, 51, 2273 (1995); V. Costantino, E. Fattorusso, and A. Mangoni, Liebigs Ann. Chem., 1995, 2133; R. Higuchi, S. Matsumoto, M. Fujita, and T. Komori, Liebigs Ann. Chem., 1995, 545; R. Higuchi, Y. Hurano, M. Mitsuyuki, R. Isobe, K. Yamada, T. Miyamoto, and T. Komori, Liebigs Ann. Chem., 1996, 593.
19. a) R. Higuchi, T. Natori, and T. Komori, Liebgs Ann. Chem., 1990, 51;
20. b) C. R. Smith, Jr., and I. A. Wolff, Lipids, 4, 9 (1968);
21. c) S. Sugiyama, M. Honda, and T. Komori, Liebigs Ann. Chem., 1988, 619;
22. d) S. Sugiyama, M. Honda, and T. Komori, Liebigs Ann. Chem., 1990, 1069.
23. Examples of total synthesis of cerebrosides containing sphingosines, see: a) R. R. Schmidt and P. Zimmemann, Angew. Chem., Int. Ed. Engl., 25, 725 (1986); K. Koike, M. Sugimoto, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 162, 237 (1987); H. Shibuya, M. Kurosu, K. Minagawa, S. Katayama, and I. Kitagawa, Chem. Pharm. Bull., 41, 1534 (1993). For a review of synthesis of sphingosines (in Japanese), see: b) T. Hino and M. Nakagawa, Farumashia, 27, 1164 (1991). For recent reports on synthesis of sphingosines, see: c) J. S. Yadav, D. Vidyanand, and D. Rajagopal, Tetrahedron Lett., 34, 1191 (1993), and references cited therein.
24. Examples of total synthesis of cerebrosides containing sphingosines, see: a) R. R. Schmidt and P. Zimmemann, Angew. Chem., Int. Ed. Engl., 25, 725 (1986); K. Koike, M. Sugimoto, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 162, 237 (1987); H. Shibuya, M. Kurosu, K. Minagawa, S. Katayama, and I. Kitagawa, Chem. Pharm. Bull., 41, 1534 (1993). For a review of synthesis of sphingosines (in Japanese), see: b) T. Hino and M. Nakagawa, Farumashia, 27, 1164 (1991). For recent reports on synthesis of sphingosines, see: c) J. S. Yadav, D. Vidyanand, and D. Rajagopal, Tetrahedron Lett., 34, 1191 (1993), and references cited therein.
25. Examples of total synthesis of cerebrosides containing sphingosines, see: a) R. R. Schmidt and P. Zimmemann, Angew. Chem., Int. Ed. Engl., 25, 725 (1986); K. Koike, M. Sugimoto, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 162, 237 (1987); H. Shibuya, M. Kurosu, K. Minagawa, S. Katayama, and I. Kitagawa, Chem. Pharm. Bull., 41, 1534 (1993). For a review of synthesis of sphingosines (in Japanese), see: b) T. Hino and M. Nakagawa, Farumashia, 27, 1164 (1991). For recent reports on synthesis of sphingosines, see: c) J. S. Yadav, D. Vidyanand, and D. Rajagopal, Tetrahedron Lett., 34, 1191 (1993), and references cited therein.
26. Examples of total synthesis of cerebrosides containing sphingosines, see: a) R. R. Schmidt and P. Zimmemann, Angew. Chem., Int. Ed. Engl., 25, 725 (1986); K. Koike, M. Sugimoto, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 162, 237 (1987); H. Shibuya, M. Kurosu, K. Minagawa, S. Katayama, and I. Kitagawa, Chem. Pharm. Bull., 41, 1534 (1993). For a review of synthesis of sphingosines (in Japanese), see: b) T. Hino and M. Nakagawa, Farumashia, 27, 1164 (1991). For recent reports on synthesis of sphingosines, see: c) J. S. Yadav, D. Vidyanand, and D. Rajagopal, Tetrahedron Lett., 34, 1191 (1993), and references cited therein.
27. Examples of total synthesis of cerebrosides containing sphingosines, see: a) R. R. Schmidt and P. Zimmemann, Angew. Chem., Int. Ed. Engl., 25, 725 (1986); K. Koike, M. Sugimoto, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 162, 237 (1987); H. Shibuya, M. Kurosu, K. Minagawa, S. Katayama, and I. Kitagawa, Chem. Pharm. Bull., 41, 1534 (1993). For a review of synthesis of sphingosines (in Japanese), see: b) T. Hino and M. Nakagawa, Farumashia, 27, 1164 (1991). For recent reports on synthesis of sphingosines, see: c) J. S. Yadav, D. Vidyanand, and D. Rajagopal, Tetrahedron Lett., 34, 1191 (1993), and references cited therein.
28. Reports on the total synthesis of cerebrosides containing phytosphingosine moieties, see: a) S. Sugiyama, M. Honda, and T. Komori, Liebigs Ann. Chem., 1990, 1063; b) M. Honda, Y. Ueda, S. Sugiyama, and T. Komori, Chem. Pharm. Bull., 39, 1385 (1991); c) K. Akimoto, T. Natori, and M. Morita, Tetrahedron Lett., 34, 5593 (1993).
29. Reports on the total synthesis of cerebrosides containing phytosphingosine moieties, see: a) S. Sugiyama, M. Honda, and T. Komori, Liebigs Ann. Chem., 1990, 1063; b) M. Honda, Y. Ueda, S. Sugiyama, and T. Komori, Chem. Pharm. Bull., 39, 1385 (1991); c) K. Akimoto, T. Natori, and M. Morita, Tetrahedron Lett., 34, 5593 (1993).
30. Reports on the total synthesis of cerebrosides containing phytosphingosine moieties, see: a) S. Sugiyama, M. Honda, and T. Komori, Liebigs Ann. Chem., 1990, 1063; b) M. Honda, Y. Ueda, S. Sugiyama, and T. Komori, Chem. Pharm. Bull., 39, 1385 (1991); c) K. Akimoto, T. Natori, and M. Morita, Tetrahedron Lett., 34, 5593 (1993).
31. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
32. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
33. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
34. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
35. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
36. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
37. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
38. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
39. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
40. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
41. For syntheses of phytosphingnsines, see: a) R. Wild and R. R. Schmidt, Liebigs Ann. Chem., 1995, 755; Y. -L. Li, X.-H. Mao, and Y.-L. Wu, J. Chem. Soc., Perkin Trans. 1, 1995, 1559; S. Kobayashi, T. Hayashi, and T. Kawasuji, Tetrahedron Lett., 35, 9573 (1994); b) T. Murakami, H. Minamikawa, and M. Hato, Tetrahedron Lett., 35, 745 (1994); c) ; R. Wild and R. R. Schmidt, Tetrahedron: Asymmetry, 5, 2195 (1994); K. Koike, Y. Nakuhara, and T. Oguwa, Agric. Biol. Chem., 54, 663 (1990); A. Dondoni, G. Funtin, M. Fogagnolo, and P. Pedrini, J. Org. Chem., 55, 1439 (1990); G. Guanti, L. Banfi, and E. Narisano, Tetrahedron Lett., 30, 5507 (1989); R. R. Schmidt and T. Maier, Carhohydr. Res., 174, 169 (1988); J. Mulzer and C. Brand, Tetrahedron, 42, 5961 (1986); J. Gigg, R. Gigg, and C. D. Warren, J. Chem. Soc. C, 1966, 1872; see also Refs. 3c and 3d.
42. For reviews of utilization of L-quebrachitol in organic synthesis, see: a) J. J. Kiddle, Chem. Rev., 95, 2189 (1995); b) N. Chida and S. Ogawa. Chem. Commun., 1997, 807.
43. For reviews of utilization of L-quebrachitol in organic synthesis, see: a) J. J. Kiddle, Chem. Rev., 95, 2189 (1995); b) N. Chida and S. Ogawa. Chem. Commun., 1997, 807.
44. S. J. Angyal and R. M. Hoskinson, Methods Carbohydr. Chem., 2, 87 (1963); S. J. Angyal and P. T. Gilham, J. Chem. Soc., 1958, 375.
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46. a) S. Murahashi, Y. Tanigawa, Y. Imada, and T. Taniguchi, J. Org. Chem., 54, 3292 (1989);
47. b) S. Murahashi, Y. Tanigawa, Y. Imada, and T. Taniguchi, Tetrahedron Lett., 27, 227 (1986).
48. Compound 4 has been utilized as a chiral starting material for the synthesis of novel sponge-derived natural product, hengamide B: see ; N. Chida, T. Tobe, K. Murai, K. Yamazaki, and S. Ogawa, Heterocycles, 38, 2383 (1994).
49. R. J. Ferrier and N. Vethaviyaser, J. Chem. Soc. C, 1971, 1907; J. S. Panek, M. Yang, and I. Muler. J. Org. Chem., 57, 4063 (1992); A. Gagneux, S. Winstein, and W. G. Young, J. Am. Chem. Soc., 82, 5956 (1960); M. Safi, R. Fahrang, and D. Sinou, Tetrahedron Lett., 31, 527 (1990); D. Askin, C. Angst, and S. J. Danishefsky, J. Org. Chem., 50, 5005 (1985); R. R. Hung, J. A. Straub, and G. M. Whitesides, J. Org. Chem., 56, 3849 (1991).
50. R. J. Ferrier and N. Vethaviyaser, J. Chem. Soc. C, 1971, 1907; J. S. Panek, M. Yang, and I. Muler. J. Org. Chem., 57, 4063 (1992); A. Gagneux, S. Winstein, and W. G. Young, J. Am. Chem. Soc., 82, 5956 (1960); M. Safi, R. Fahrang, and D. Sinou, Tetrahedron Lett., 31, 527 (1990); D. Askin, C. Angst, and S. J. Danishefsky, J. Org. Chem., 50, 5005 (1985); R. R. Hung, J. A. Straub, and G. M. Whitesides, J. Org. Chem., 56, 3849 (1991).
51. R. J. Ferrier and N. Vethaviyaser, J. Chem. Soc. C, 1971, 1907; J. S. Panek, M. Yang, and I. Muler. J. Org. Chem., 57, 4063 (1992); A. Gagneux, S. Winstein, and W. G. Young, J. Am. Chem. Soc., 82, 5956 (1960); M. Safi, R. Fahrang, and D. Sinou, Tetrahedron Lett., 31, 527 (1990); D. Askin, C. Angst, and S. J. Danishefsky, J. Org. Chem., 50, 5005 (1985); R. R. Hung, J. A. Straub, and G. M. Whitesides, J. Org. Chem., 56, 3849 (1991).
52. R. J. Ferrier and N. Vethaviyaser, J. Chem. Soc. C, 1971, 1907; J. S. Panek, M. Yang, and I. Muler. J. Org. Chem., 57, 4063 (1992); A. Gagneux, S. Winstein, and W. G. Young, J. Am. Chem. Soc., 82, 5956 (1960); M. Safi, R. Fahrang, and D. Sinou, Tetrahedron Lett., 31, 527 (1990); D. Askin, C. Angst, and S. J. Danishefsky, J. Org. Chem., 50, 5005 (1985); R. R. Hung, J. A. Straub, and G. M. Whitesides, J. Org. Chem., 56, 3849 (1991).
53. R. J. Ferrier and N. Vethaviyaser, J. Chem. Soc. C, 1971, 1907; J. S. Panek, M. Yang, and I. Muler. J. Org. Chem., 57, 4063 (1992); A. Gagneux, S. Winstein, and W. G. Young, J. Am. Chem. Soc., 82, 5956 (1960); M. Safi, R. Fahrang, and D. Sinou, Tetrahedron Lett., 31, 527 (1990); D. Askin, C. Angst, and S. J. Danishefsky, J. Org. Chem., 50, 5005 (1985); R. R. Hung, J. A. Straub, and G. M. Whitesides, J. Org. Chem., 56, 3849 (1991).
54. R. J. Ferrier and N. Vethaviyaser, J. Chem. Soc. C, 1971, 1907; J. S. Panek, M. Yang, and I. Muler. J. Org. Chem., 57, 4063 (1992); A. Gagneux, S. Winstein, and W. G. Young, J. Am. Chem. Soc., 82, 5956 (1960); M. Safi, R. Fahrang, and D. Sinou, Tetrahedron Lett., 31, 527 (1990); D. Askin, C. Angst, and S. J. Danishefsky, J. Org. Chem., 50, 5005 (1985); R. R. Hung, J. A. Straub, and G. M. Whitesides, J. Org. Chem., 56, 3849 (1991).
55. For a report on synthesis of racemic conduramine F-4, see: a) M. Nakajima, A. Hasegawa, and N. Kurihara, Chem. Ber., 95, 2708 (1962). For a review of conduritols and related compounds, see: b) M. Balci, Y. Sütbeyaz, and H. Seçen, Tetrahedron, 46, 3715 (1990). For a report on biological activity of conduritols, see: c) G. Legler and E. Bause, Carbohydr. Res., 28, 45 (1973). Reports on preparation of racemic conduramine F-1, see: d) G. Kresze and W. Dittel, Liebigs Ann. Chem., 1981, 610. Preparation of (+)-conduramine A-1: O. Werbitzky, K. Klier, and H. Felber, Liebigs Ann. Chem., 1990, 267; (+)-conduramine F-1: F. H. Paulsen, W. Röben, and F. R. Heiker, Chem. Ber., 114, 3242 (1981).
56. For a report on synthesis of racemic conduramine F-4, see: a) M. Nakajima, A. Hasegawa, and N. Kurihara, Chem. Ber., 95, 2708 (1962). For a review of conduritols and related compounds, see: b) M. Balci, Y. Sütbeyaz, and H. Seçen, Tetrahedron, 46, 3715 (1990). For a report on biological activity of conduritols, see: c) G. Legler and E. Bause, Carbohydr. Res., 28, 45 (1973). Reports on preparation of racemic conduramine F-1, see: d) G. Kresze and W. Dittel, Liebigs Ann. Chem., 1981, 610. Preparation of (+)-conduramine A-1: O. Werbitzky, K. Klier, and H. Felber, Liebigs Ann. Chem., 1990, 267; (+)-conduramine F-1: F. H. Paulsen, W. Röben, and F. R. Heiker, Chem. Ber., 114, 3242 (1981).
57. For a report on synthesis of racemic conduramine F-4, see: a) M. Nakajima, A. Hasegawa, and N. Kurihara, Chem. Ber., 95, 2708 (1962). For a review of conduritols and related compounds, see: b) M. Balci, Y. Sütbeyaz, and H. Seçen, Tetrahedron, 46, 3715 (1990). For a report on biological activity of conduritols, see: c) G. Legler and E. Bause, Carbohydr. Res., 28, 45 (1973). Reports on preparation of racemic conduramine F-1, see: d) G. Kresze and W. Dittel, Liebigs Ann. Chem., 1981, 610. Preparation of (+)-conduramine A-1: O. Werbitzky, K. Klier, and H. Felber, Liebigs Ann. Chem., 1990, 267; (+)-conduramine F-1: F. H. Paulsen, W. Röben, and F. R. Heiker, Chem. Ber., 114, 3242 (1981).
58. For a report on synthesis of racemic conduramine F-4, see: a) M. Nakajima, A. Hasegawa, and N. Kurihara, Chem. Ber., 95, 2708 (1962). For a review of conduritols and related compounds, see: b) M. Balci, Y. Sütbeyaz, and H. Seçen, Tetrahedron, 46, 3715 (1990). For a report on biological activity of conduritols, see: c) G. Legler and E. Bause, Carbohydr. Res., 28, 45 (1973). Reports on preparation of racemic conduramine F-1, see: d) G. Kresze and W. Dittel, Liebigs Ann. Chem., 1981, 610. Preparation of (+)-conduramine A-1: O. Werbitzky, K. Klier, and H. Felber, Liebigs Ann. Chem., 1990, 267; (+)-conduramine F-1: F. H. Paulsen, W. Röben, and F. R. Heiker, Chem. Ber., 114, 3242 (1981).
59. For a report on synthesis of racemic conduramine F-4, see: a) M. Nakajima, A. Hasegawa, and N. Kurihara, Chem. Ber., 95, 2708 (1962). For a review of conduritols and related compounds, see: b) M. Balci, Y. Sütbeyaz, and H. Seçen, Tetrahedron, 46, 3715 (1990). For a report on biological activity of conduritols, see: c) G. Legler and E. Bause, Carbohydr. Res., 28, 45 (1973). Reports on preparation of racemic conduramine F-1, see: d) G. Kresze and W. Dittel, Liebigs Ann. Chem., 1981, 610. Preparation of (+)-conduramine A-1: O. Werbitzky, K. Klier, and H. Felber, Liebigs Ann. Chem., 1990, 267; (+)-conduramine F-1: F. H. Paulsen, W. Röben, and F. R. Heiker, Chem. Ber., 114, 3242 (1981).
60. For a report on synthesis of racemic conduramine F-4, see: a) M. Nakajima, A. Hasegawa, and N. Kurihara, Chem. Ber., 95, 2708 (1962). For a review of conduritols and related compounds, see: b) M. Balci, Y. Sütbeyaz, and H. Seçen, Tetrahedron, 46, 3715 (1990). For a report on biological activity of conduritols, see: c) G. Legler and E. Bause, Carbohydr. Res., 28, 45 (1973). Reports on preparation of racemic conduramine F-1, see: d) G. Kresze and W. Dittel, Liebigs Ann. Chem., 1981, 610. Preparation of (+)-conduramine A-1: O. Werbitzky, K. Klier, and H. Felber, Liebigs Ann. Chem., 1990, 267; (+)-conduramine F-1: F. H. Paulsen, W. Röben, and F. R. Heiker, Chem. Ber., 114, 3242 (1981).
61. J.M. Klunder and G. H. Posner, in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 3, pp. 207-239; B. H. Lipshutz, in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 1, pp. 107-138; B. H. Lipshutz and S. Sengupta, Org. React., 41, 135 (1992).
62. J.M. Klunder and G. H. Posner, in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 3, pp. 207-239; B. H. Lipshutz, in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 1, pp. 107-138; B. H. Lipshutz and S. Sengupta, Org. React., 41, 135 (1992).
63. J.M. Klunder and G. H. Posner, in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 3, pp. 207-239; B. H. Lipshutz, in "Comprehensive Organic Synthesis," ed by B. M. Trost, Pergamon Press, Oxford (1991), Vol. 1, pp. 107-138; B. H. Lipshutz and S. Sengupta, Org. React., 41, 135 (1992).
64. a) B. J. Wakefield, "Organomagnesium Methods in Organic Synthesis," Academic Press, London (1995), pp. 165-168 and 62-70;
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68. This compound had been synthesized from (2E,4R)-2-hexadecen-4-ol by Komori, see: Ref. 3c.
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