Alkenylzinc-Mediated Approach to the Vitamin D Skeleton. Application to the Synthesis of 6-Methyl Analogs of Vitamin and Previtamin D

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6353-6358

  García, Ana M ^a   Mascareñas, José L ^a   Castedo, Luis ^a   Mouriño, Antonio ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000513376     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970605m     Document Type: Article

References (69)

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11. In recent years, a wide range of analogs of 1 with weak calcemic effects have been prepared, some of which have been shown to be promising drugs for the treatment of psoriasis and certain cancers: (a) Ikekawa, N. Med. Chem. Rev. 1987, 7, 333. (b) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. (c) Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Prahl, J.; Schnoes, H. K.; DeLuca, H. F. J. Biol. Chem. 1987, 262, 14164. (d) Shiuey, S. J.; Partridge, J. J.; Uskokovic, M. R. J. Org. Chem. 1988, 53, 1040. (e) Zhou, J.; Norman, A. W.; Lubbert, M.; Collins, E. D.; Uskokovic, M. R.; Koeffler, H. P. Blood 1989, 74, 82. (f) Perlman, R. R.; Sicinski, H. K.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823. (g) Figadere, B.; Norman, A. W.; Henry, H. L.; Koeffler, H. P.; Zhou, J.-Y.; Okamura, W. H. J. Med. Chem. 1991, 34, 2452. (h) Kissmeyer, A.-M.; Binderup. L. Biochem. Pharmacol. 1991, 42, 1601. (i) Zhou, J.-Y; Norman, A. W.; Akashi, M.; Chen, D.-L.; Uskokovic, M. R.; Aurrecoechea, J. M.; Dauben, W. H.; Okamura, W. H.; Koeffler, H. P. Blood 1991, 78, 75. (j) Binderup, L. Biorg. Med. Chem. Lett. 1993, 3, 1891.
12. In recent years, a wide range of analogs of 1 with weak calcemic effects have been prepared, some of which have been shown to be promising drugs for the treatment of psoriasis and certain cancers: (a) Ikekawa, N. Med. Chem. Rev. 1987, 7, 333. (b) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. (c) Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Prahl, J.; Schnoes, H. K.; DeLuca, H. F. J. Biol. Chem. 1987, 262, 14164. (d) Shiuey, S. J.; Partridge, J. J.; Uskokovic, M. R. J. Org. Chem. 1988, 53, 1040. (e) Zhou, J.; Norman, A. W.; Lubbert, M.; Collins, E. D.; Uskokovic, M. R.; Koeffler, H. P. Blood 1989, 74, 82. (f) Perlman, R. R.; Sicinski, H. K.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823. (g) Figadere, B.; Norman, A. W.; Henry, H. L.; Koeffler, H. P.; Zhou, J.-Y.; Okamura, W. H. J. Med. Chem. 1991, 34, 2452. (h) Kissmeyer, A.-M.; Binderup. L. Biochem. Pharmacol. 1991, 42, 1601. (i) Zhou, J.-Y; Norman, A. W.; Akashi, M.; Chen, D.-L.; Uskokovic, M. R.; Aurrecoechea, J. M.; Dauben, W. H.; Okamura, W. H.; Koeffler, H. P. Blood 1991, 78, 75. (j) Binderup, L. Biorg. Med. Chem. Lett. 1993, 3, 1891.
13. In recent years, a wide range of analogs of 1 with weak calcemic effects have been prepared, some of which have been shown to be promising drugs for the treatment of psoriasis and certain cancers: (a) Ikekawa, N. Med. Chem. Rev. 1987, 7, 333. (b) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. (c) Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Prahl, J.; Schnoes, H. K.; DeLuca, H. F. J. Biol. Chem. 1987, 262, 14164. (d) Shiuey, S. J.; Partridge, J. J.; Uskokovic, M. R. J. Org. Chem. 1988, 53, 1040. (e) Zhou, J.; Norman, A. W.; Lubbert, M.; Collins, E. D.; Uskokovic, M. R.; Koeffler, H. P. Blood 1989, 74, 82. (f) Perlman, R. R.; Sicinski, H. K.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823. (g) Figadere, B.; Norman, A. W.; Henry, H. L.; Koeffler, H. P.; Zhou, J.-Y.; Okamura, W. H. J. Med. Chem. 1991, 34, 2452. (h) Kissmeyer, A.-M.; Binderup. L. Biochem. Pharmacol. 1991, 42, 1601. (i) Zhou, J.-Y; Norman, A. W.; Akashi, M.; Chen, D.-L.; Uskokovic, M. R.; Aurrecoechea, J. M.; Dauben, W. H.; Okamura, W. H.; Koeffler, H. P. Blood 1991, 78, 75. (j) Binderup, L. Biorg. Med. Chem. Lett. 1993, 3, 1891.
14. In recent years, a wide range of analogs of 1 with weak calcemic effects have been prepared, some of which have been shown to be promising drugs for the treatment of psoriasis and certain cancers: (a) Ikekawa, N. Med. Chem. Rev. 1987, 7, 333. (b) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. (c) Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Prahl, J.; Schnoes, H. K.; DeLuca, H. F. J. Biol. Chem. 1987, 262, 14164. (d) Shiuey, S. J.; Partridge, J. J.; Uskokovic, M. R. J. Org. Chem. 1988, 53, 1040. (e) Zhou, J.; Norman, A. W.; Lubbert, M.; Collins, E. D.; Uskokovic, M. R.; Koeffler, H. P. Blood 1989, 74, 82. (f) Perlman, R. R.; Sicinski, H. K.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823. (g) Figadere, B.; Norman, A. W.; Henry, H. L.; Koeffler, H. P.; Zhou, J.-Y.; Okamura, W. H. J. Med. Chem. 1991, 34, 2452. (h) Kissmeyer, A.-M.; Binderup. L. Biochem. Pharmacol. 1991, 42, 1601. (i) Zhou, J.-Y; Norman, A. W.; Akashi, M.; Chen, D.-L.; Uskokovic, M. R.; Aurrecoechea, J. M.; Dauben, W. H.; Okamura, W. H.; Koeffler, H. P. Blood 1991, 78, 75. (j) Binderup, L. Biorg. Med. Chem. Lett. 1993, 3, 1891.
15. In recent years, a wide range of analogs of 1 with weak calcemic effects have been prepared, some of which have been shown to be promising drugs for the treatment of psoriasis and certain cancers: (a) Ikekawa, N. Med. Chem. Rev. 1987, 7, 333. (b) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. (c) Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Prahl, J.; Schnoes, H. K.; DeLuca, H. F. J. Biol. Chem. 1987, 262, 14164. (d) Shiuey, S. J.; Partridge, J. J.; Uskokovic, M. R. J. Org. Chem. 1988, 53, 1040. (e) Zhou, J.; Norman, A. W.; Lubbert, M.; Collins, E. D.; Uskokovic, M. R.; Koeffler, H. P. Blood 1989, 74, 82. (f) Perlman, R. R.; Sicinski, H. K.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823. (g) Figadere, B.; Norman, A. W.; Henry, H. L.; Koeffler, H. P.; Zhou, J.-Y.; Okamura, W. H. J. Med. Chem. 1991, 34, 2452. (h) Kissmeyer, A.-M.; Binderup. L. Biochem. Pharmacol. 1991, 42, 1601. (i) Zhou, J.-Y; Norman, A. W.; Akashi, M.; Chen, D.-L.; Uskokovic, M. R.; Aurrecoechea, J. M.; Dauben, W. H.; Okamura, W. H.; Koeffler, H. P. Blood 1991, 78, 75. (j) Binderup, L. Biorg. Med. Chem. Lett. 1993, 3, 1891.
16. In recent years, a wide range of analogs of 1 with weak calcemic effects have been prepared, some of which have been shown to be promising drugs for the treatment of psoriasis and certain cancers: (a) Ikekawa, N. Med. Chem. Rev. 1987, 7, 333. (b) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. (c) Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Prahl, J.; Schnoes, H. K.; DeLuca, H. F. J. Biol. Chem. 1987, 262, 14164. (d) Shiuey, S. J.; Partridge, J. J.; Uskokovic, M. R. J. Org. Chem. 1988, 53, 1040. (e) Zhou, J.; Norman, A. W.; Lubbert, M.; Collins, E. D.; Uskokovic, M. R.; Koeffler, H. P. Blood 1989, 74, 82. (f) Perlman, R. R.; Sicinski, H. K.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823. (g) Figadere, B.; Norman, A. W.; Henry, H. L.; Koeffler, H. P.; Zhou, J.-Y.; Okamura, W. H. J. Med. Chem. 1991, 34, 2452. (h) Kissmeyer, A.-M.; Binderup. L. Biochem. Pharmacol. 1991, 42, 1601. (i) Zhou, J.-Y; Norman, A. W.; Akashi, M.; Chen, D.-L.; Uskokovic, M. R.; Aurrecoechea, J. M.; Dauben, W. H.; Okamura, W. H.; Koeffler, H. P. Blood 1991, 78, 75. (j) Binderup, L. Biorg. Med. Chem. Lett. 1993, 3, 1891.
17. In recent years, a wide range of analogs of 1 with weak calcemic effects have been prepared, some of which have been shown to be promising drugs for the treatment of psoriasis and certain cancers: (a) Ikekawa, N. Med. Chem. Rev. 1987, 7, 333. (b) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. (c) Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Prahl, J.; Schnoes, H. K.; DeLuca, H. F. J. Biol. Chem. 1987, 262, 14164. (d) Shiuey, S. J.; Partridge, J. J.; Uskokovic, M. R. J. Org. Chem. 1988, 53, 1040. (e) Zhou, J.; Norman, A. W.; Lubbert, M.; Collins, E. D.; Uskokovic, M. R.; Koeffler, H. P. Blood 1989, 74, 82. (f) Perlman, R. R.; Sicinski, H. K.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823. (g) Figadere, B.; Norman, A. W.; Henry, H. L.; Koeffler, H. P.; Zhou, J.-Y.; Okamura, W. H. J. Med. Chem. 1991, 34, 2452. (h) Kissmeyer, A.-M.; Binderup. L. Biochem. Pharmacol. 1991, 42, 1601. (i) Zhou, J.-Y; Norman, A. W.; Akashi, M.; Chen, D.-L.; Uskokovic, M. R.; Aurrecoechea, J. M.; Dauben, W. H.; Okamura, W. H.; Koeffler, H. P. Blood 1991, 78, 75. (j) Binderup, L. Biorg. Med. Chem. Lett. 1993, 3, 1891.
18. In recent years, a wide range of analogs of 1 with weak calcemic effects have been prepared, some of which have been shown to be promising drugs for the treatment of psoriasis and certain cancers: (a) Ikekawa, N. Med. Chem. Rev. 1987, 7, 333. (b) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. (c) Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Prahl, J.; Schnoes, H. K.; DeLuca, H. F. J. Biol. Chem. 1987, 262, 14164. (d) Shiuey, S. J.; Partridge, J. J.; Uskokovic, M. R. J. Org. Chem. 1988, 53, 1040. (e) Zhou, J.; Norman, A. W.; Lubbert, M.; Collins, E. D.; Uskokovic, M. R.; Koeffler, H. P. Blood 1989, 74, 82. (f) Perlman, R. R.; Sicinski, H. K.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823. (g) Figadere, B.; Norman, A. W.; Henry, H. L.; Koeffler, H. P.; Zhou, J.-Y.; Okamura, W. H. J. Med. Chem. 1991, 34, 2452. (h) Kissmeyer, A.-M.; Binderup. L. Biochem. Pharmacol. 1991, 42, 1601. (i) Zhou, J.-Y; Norman, A. W.; Akashi, M.; Chen, D.-L.; Uskokovic, M. R.; Aurrecoechea, J. M.; Dauben, W. H.; Okamura, W. H.; Koeffler, H. P. Blood 1991, 78, 75. (j) Binderup, L. Biorg. Med. Chem. Lett. 1993, 3, 1891.
19. In recent years, a wide range of analogs of 1 with weak calcemic effects have been prepared, some of which have been shown to be promising drugs for the treatment of psoriasis and certain cancers: (a) Ikekawa, N. Med. Chem. Rev. 1987, 7, 333. (b) Abe, J.; Morikawa, M.; Miyamoto, K.; Kaiho, S.; Fukushima, M.; Miyaura, C.; Abe, E.; Suda, T.; Nishii, Y. FEBS Lett. 1987, 226, 58. (c) Ostrem, V. K.; Lau, W. F.; Lee, S. H.; Perlman, K.; Prahl, J.; Schnoes, H. K.; DeLuca, H. F. J. Biol. Chem. 1987, 262, 14164. (d) Shiuey, S. J.; Partridge, J. J.; Uskokovic, M. R. J. Org. Chem. 1988, 53, 1040. (e) Zhou, J.; Norman, A. W.; Lubbert, M.; Collins, E. D.; Uskokovic, M. R.; Koeffler, H. P. Blood 1989, 74, 82. (f) Perlman, R. R.; Sicinski, H. K.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823. (g) Figadere, B.; Norman, A. W.; Henry, H. L.; Koeffler, H. P.; Zhou, J.-Y.; Okamura, W. H. J. Med. Chem. 1991, 34, 2452. (h) Kissmeyer, A.-M.; Binderup. L. Biochem. Pharmacol. 1991, 42, 1601. (i) Zhou, J.-Y; Norman, A. W.; Akashi, M.; Chen, D.-L.; Uskokovic, M. R.; Aurrecoechea, J. M.; Dauben, W. H.; Okamura, W. H.; Koeffler, H. P. Blood 1991, 78, 75. (j) Binderup, L. Biorg. Med. Chem. Lett. 1993, 3, 1891.
20. For recent reviews, see: (a) Dai, H.; Posner, G. H. Synthesis 1994, 1383. (b) Schmalz, H.-G. Nachr. Chem. Tech. Lab. 1994, 42, 397. (c) Znu, G. D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877.
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34. Although the conjugated triene system of natural vitamin D is believed to be necessary for biological activity, there has been little research into the biological effect of modifying this triene system. However, several substituted derivatives have been synthesized and shown to have interesting activities: (a) Wilhelm, F.; Dauben, W. G.; Kohler, B.; Roesle, A.; Norman, A. W. Arch. Biochem. Biophys. 1984, 233, 127. (b) Gray, T. K.; Millington, D. S.; Maltby, D. A.; Williams, M. E.; Cohen, M. S.; Dodd, R. C. Proc. Nat. Acad. Sci. U.S.A. 1985, 82, 8218. (c) Shiina, Y. Y.; Miyaura, C.; Tanaka, H.; Abe, E.; Yamada, S.; Yamamoto, K.; Ino, E.; Takayama, H.; Matsunaga, I.; Nishii, Y.; Suda, T. J. Med. Chem. 1985, 28, 1153. (d) Steinmeyer, A.; Neef, G. Tetrahedron Lett. 1992, 33, 4879.
35. Although the conjugated triene system of natural vitamin D is believed to be necessary for biological activity, there has been little research into the biological effect of modifying this triene system. However, several substituted derivatives have been synthesized and shown to have interesting activities: (a) Wilhelm, F.; Dauben, W. G.; Kohler, B.; Roesle, A.; Norman, A. W. Arch. Biochem. Biophys. 1984, 233, 127. (b) Gray, T. K.; Millington, D. S.; Maltby, D. A.; Williams, M. E.; Cohen, M. S.; Dodd, R. C. Proc. Nat. Acad. Sci. U.S.A. 1985, 82, 8218. (c) Shiina, Y. Y.; Miyaura, C.; Tanaka, H.; Abe, E.; Yamada, S.; Yamamoto, K.; Ino, E.; Takayama, H.; Matsunaga, I.; Nishii, Y.; Suda, T. J. Med. Chem. 1985, 28, 1153. (d) Steinmeyer, A.; Neef, G. Tetrahedron Lett. 1992, 33, 4879.
36. Although the conjugated triene system of natural vitamin D is believed to be necessary for biological activity, there has been little research into the biological effect of modifying this triene system. However, several substituted derivatives have been synthesized and shown to have interesting activities: (a) Wilhelm, F.; Dauben, W. G.; Kohler, B.; Roesle, A.; Norman, A. W. Arch. Biochem. Biophys. 1984, 233, 127. (b) Gray, T. K.; Millington, D. S.; Maltby, D. A.; Williams, M. E.; Cohen, M. S.; Dodd, R. C. Proc. Nat. Acad. Sci. U.S.A. 1985, 82, 8218. (c) Shiina, Y. Y.; Miyaura, C.; Tanaka, H.; Abe, E.; Yamada, S.; Yamamoto, K.; Ino, E.; Takayama, H.; Matsunaga, I.; Nishii, Y.; Suda, T. J. Med. Chem. 1985, 28, 1153. (d) Steinmeyer, A.; Neef, G. Tetrahedron Lett. 1992, 33, 4879.
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49. The greater stability of this conformation is consistent with molecular mechanics calculations (MMX).
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