Total synthesis of 25-hydroxy vitamin D3 northern portion, involving tandem conjugate additions

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2218-2223

  Marczak, Stanislaw ^a   Michalak, Karol ^a   Urbańczyk Lipkowska, Zofia ^a   Wicha, Jerzy ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CALCITRIOL DERIVATIVE; VITAMIN D DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

EID: 0032478776     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971967x     Document Type: Article

References (51)

1. Bouillon, R.; Okamura, W. H. Norman, A. W. Endocrine Rev. 1995, 16, 200-257.
2. Connor, R. I.; Rigby, W. F. C. Biochem. Biophys. Res. Commun. 1991, 176, 852-859.
3. Cantorna, M. T.; Hayes, C. E.; DeLuca, H. F. Proc. Nat. Acad. Sci. U.S.A. 1996, 93, 7861-7864.
4. For recent reviews, see: (a) Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952.
5. (b) Dai, H.; Posner, G. H. Synthesis 1994, 1383-1398.
6. (c) Tachibana, Y.; Tsuji M. in Studies in Natural Products Chemistry; Ur-Rahman, A., Ed.; Elsevier: Amsterdam, 1992; Vol. 11, pp 379-408.
7. (d) Wilson, S. R.; Yasmin, A. Ibid. 1992; Vol. 10, pp 43-75.
8. Grzywacz, P.; Marczak, S.; Wicha, J. J. Org. Chem. 1997, 62, 5293-5298.
9. (a) Narasaka, K.; Soai, K.; Mukaiyama, T. Chem. Lett. 1974, 1223-1224.
10. (b) Mukaiyama, T. Challenges in Synthetic Organic Chemistry, Clarendon Press: Oxford, 1990 and references therein.
11. (a) Hagiwara, H.; Okano, A.; Uda, H. J. Chem. Soc., Chem. Commun. 1985, 1047.
12. (b) Mukaiyama, T.; Sagawa, Y.; Kobayashi, S. Chem. Lett. 1986, 1821-1824.
13. (c) Hagiwara, H.; Okano, A.; Akama, T.; Uda, H. J. Chem. Soc., Chem. Commun. 1987, 1333-1335.
14. (d) Hagiwara, H.; Akama, T.; Okano, A.; Uda, H. Chem. Lett. 1989, 2149-2152.
15. (e) Ihara, M.; Suzuki, S.; Taniguchi, N.; Fukumoto, K. Kabuto, Ch. J. Chem. Soc., Perkin Trans. 1 1992, 2527-2530.
16. A preliminary communication from this work has been published: Marczak, S.; Michalak, K.; Wicha, J. Tetrahedron Lett. 1995, 36, 5425-5428.
17. For a simple procedure for preparation of this compound, see: Marczak, S.; Michalak, K.; Wicha, J. Pol. J. Chem. 1994, 68, 321-322.
18. (a) Kobayashi, S.; Murakami, M.; Mukaiyama, T. Chem. Lett. 1985, 953-956.
19. (b) Mukaiyama, T.; Tamura, M.; Kobayashi, S. Chem. Lett. 1987, 743-746.
20. (a) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Tetrahedron Organic Chemistry Series, No. 9; Pergamon Press: Oxford, 1992.
21. (b) Jung, M. E. in Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, Chapter 1.1.
22. (c) Sato, T.; Wakahara, Y.; Otera, J.; Nozaki, H. Tetrahedron 1991, 47, 9773-9782.
23. (d) Duhamel, P.; Dujardin, G.; Hennequin, L.; Poirier, J.-M. J. Chem. Soc., Perkin Trans. 1, 1992, 387-396.
24. (e) Ranu, B. C.; Saha, M.; Bhar, S. Tetrahedron Lett. 1993, 34, 1989-1990.
25. (a) Stork, G. Ganem, B. J. Am. Chem. Soc. 1973, 95, 6152-6153.
26. (b) Boeckman, R. K., Jr. J. Am. Chem. Soc. 1973, 95, 6867-6868. See also: Haynes, R. K.; Vonwiller, S. C.; Hambley, T. W. J. Org. Chem. 1989, 54, 5162-5970.
27. (b) Boeckman, R. K., Jr. J. Am. Chem. Soc. 1973, 95, 6867-6868. See also: Haynes, R. K.; Vonwiller, S. C.; Hambley, T. W. J. Org. Chem. 1989, 54, 5162-5970.
28. Dancer, R. J.; Haynes, R. K.; Loughlin, W. A.; Vonwiller, S. C. Aust. J. Chem. 1990, 43, 1375-1389.
29. (a) Narasaka, K.; Soai, K.; Aikawa, Y.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1976, 49, 779-783.
30. (b) Huffman, J. W.; Potnis, S. M.; Satish, A. V. J. Org. Chem. 1985, 50, 4266-4270.
31. (c) Tanaka, M.; Suemune, H.; Sakai, K.; Tetrahedron Lett. 1988, 29, 1733-1736.
32. The crystallographic data are available in the Supporing Information.
33. (a) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji J. Tetrahedron 1993, 49, 5483-5493.
34. (b) Mandai, T.; Matsumoto, T.; Kawada, M.; Tsuji J. J. Org. Chem. 1992, 57, 1326-1327.
35. Tietze, L. F.; Subba Rao, P. S. V. Synlett 1993, 291-292.
36. Michalak, K.; Wicha, J. Unpublished results.
37. 4 or K/Na alloy failed.
38. Lythgoe, B.; Roberts, D. A.; Waterhouse, I. J. Chem. Soc., Perkin Trans. 1 1977, 2608-2612.
39. (a) Brockmann, H.; Busse, A. Z. Z. Physiol. Chem. 1938, 256, 252-270.
40. (b) Inhoffen, H. H.; Quinkert, G.; Seigismund, S.; Kampe, D.; Domagk, G. F. Chem. Ber. 1957, 90, 664-673.
41. (c) Condran, P. J.; Hammond, M. L.; Mouniño, A.; Okamura, W. H. J. Am. Chem. Soc. 1980, 102, 6259-6267.
42. Kocienski, P. J.; Lythgoe, B. J. Chem. Soc., Perkin Trans. 1 1979, 1290-1293.
43. (a) Camps, F.; Coll, J.; Messeguer, A.; Pericǎs, M. A. Tetrahedron Lett. 1981, 22, 3895-3896.
44. (b) Camps, F.; Coll, J.; Messeguer, A.; Pujol, F. J. Org. Chem. 1982, 47, 5402-5404.
45. (c) Amann, A.; Ourisson, G.; Luu, B. Synthesis 1987, 696-700.
46. Kishi, Y.; Aratani, M.; Tanino, H.; Fukayama, T.; Goto, T. J. Chem. Soc., Chem. Commun. 1972, 64-65.
47. 3N and then with hexane.
48. In the text vitamin D (steroid) numbering is used; however, in the Experimental Section compounds are named according to IUPAC nomenclature. IUPAC names were generated with the aid of the Beilstein AutoNom program.
49. Hahn, E. F. J. Org. Chem. 1973, 38, 2092-2094.
50. 2O (13 mL, 130 mmol), stirred at 0 °C, was added formic acid (100%, 6 mL, 159 mmol). The mixture was stirred at 60 °C for 2 h and cooled and stored under argon.
51. Michalak, K.; Stepanenko, W.; Wicha, J. Tetrahedron Lett. 1996, 37, 7657-7658.