Synthesis of spiro[4.5]decane CF-ring analogues of 1α,25- dihydroxyvitamin D3

Organic Letters

Volumn 8, Issue 19, 2006, Pages 4247-4250

  Schepens, Wim ^a   Van Haver, Dirk ^a   Vandewalle, Maurits ^a   Bouillon, Roger ^b   Verstuyf, Annemieke ^b   De Clercq, Pierre J ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; CALCITRIOL; DECANE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ALKANES; CALCITRIOL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33749014643     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061575p     Document Type: Article

References (43)

1. (a) Proceedings of the 12th Workshop on Vitamin D: Bouillon, R.; Norman, A. W.; Pasqualini, J. R., Eds. J. Steroid Biochem. Mol. Biol. 2004, 89-90, 1-633, and the previous 11 volumes in this series,
2. (b) Vitamin D; Feldman, D., Glorieux, F. H., Eds.; Academic Press: San Diego, CA, 1997; 1285 pages.
3. (a) Nagpal, S.; Na, S.; Rathnachalam, R. Endocr. Rev. 2005, 26, 662-687.
4. (b) Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200-257.
5. (a) Posner, G. H.; Kahraman, M. Eur. J. Org. Chem. 2000, 3889-3895.
6. (b) Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952.
7. (c) Dai, H.; Posner, G. H. Synthesis 1994, 1383-1398.
8. (a) Bouillon, R.; Verlinden, L.; Eelen, G.; De Clercq, P.; Vandewalle, M.; Mathieu, C.; Verstuyf, A. J. Steroid Biochem. Mol. Biol. 2005, 97, 21-30.
9. (b) Chen, Y.-J.; Gao, L.-J.; Murad, I.; Verstuyf, A.; Verlinden, L.; Verboven, C.; Bouillon, R.; Viterbo, D.; Milanesio, M.; Van Haver, D.; Vandewalle, M.; De Clercq, P. J. Org. Biomol. Chem. 2003, 1, 257-267, and references therein.
10. (c) Bouillon, R.; Vandewalle, M.; De Clercq, P. J., patent PCT Int. Publ. No. WO 95/01960 (1995); CAN 122: 314933.
11. For spiro[5.5]undecane analogues, see: Schepens, W.; Van Haver, D.; Vandewalle, M.; De Clercq, P. J.; Bouillon, R.; Verstuyf, A. Bioorg. Med. Chem. Lett. 2004, 14, 3889-3892.
12. Epimerization at C-20 often generates analogues with enhanced biological activity, see: Binderup, L.; Latini, S.; Binderup, E.; Bretting, C.; Calverley, M.; Hansen, K. Biochem. Pharmacol. 1991, 42, 1569-1575.
13. Removal of C-19 usually leads to a reduction of calcemic activity, see: Perlman, K. L.; Sicinski, R. R.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1990, 31, 1823-1824.
14. (a) Gabriëls, S.; Van Haver, D.; Vandewalle, M.; De Clercq, P.; Verstuyf, A.; Bouillon, R. Chem. Eur. J. 2001, 7, 520-532.
15. (b) Zhou, X.; Zhu, G.-D.; Van Haver, D.; Vandewalle, M.; De Clercq, P. J.; Verstuyf, A.; Bouillon, R. J. Med. Chem. 1999, 42, 3539-3556.
16. (c) Van Haver, D.; De Clercq, P. J. Bioorg. Med. Chem. Lett. 1998, 8, 1029-1034.
17. (d) Yamada, S.; Yamamoto, K.; Masuno, H.; Ohta, M. J. Med. Chem. 1998, 41, 1467-1475.
18. (a) Bouillon, R.; Sarandeses, L. A.; Allewaert, K.; Zhao, J.; Mascareñas, J. L.; Mouriño A.; Vrielynck, S.; De Clercq, P.; Vandewalle, M. J. Bone Miner. Res. 1993, 8, 1009-1015.
19. (b) Havinga, E. Experientia 1973, 29, 1181-1193.
20. (a) Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. J. Org. Chem. 1986, 51, 3098-3108.
21. (b) Lythgoe, B.; Moran, T. A.; Nambudiry, M. E. N.; Ruston, S.; Tideswell, J.; Wright, P. W. J. Chem. Soc., Perkin Trans. 1 1978, 590-595.
22. For previous syntheses of racemic 4, see: (a) Godleski, S. A.; Valpey, R. S. J. Org. Chem. 1982, 47, 381-384.
23. (b) Trost, B. M.; Murayama, E. J. Am. Chem. Soc. 1981, 103, 6529-6530.
24. For examples of the enantioselective construction of quaternary stereogenic carbon centers, see: (a) Breit, B.; Demel, P.; Studte, C. Angew. Chem., Int. Ed. 2004, 43, 3786-3789.
25. (b) Christoffers, J.; Mann, A. Angew. Chem., Int. Ed. 2001, 40, 4591-4597.
26. (c) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388-401.
27. (d) Fuji, K. Chem. Rev. 1993, 93, 2037-2066.
28. For the synthesis of spirocyclic systems, see: (a) Pradhan, R.; Patra, M.; Behera, A. K.; Mishra, B. K.; Behera, R. K. Tetrahedron 2006, 62, 779-828.
29. (b) Sannigrahi, M. Tetrahedron 1999, 55, 9007-9071.
30. For a sequential Claisen/ring-closing metathesis approach to spirocyclic cyclopentanes and cyclohexanes, see: Beaulieu, P.; Ogilvie, W. W. Tetrahedron Lett. 2003, 44, 8883-8885.
31. (a) He, F.; Bo, Y.; Altom, J. D.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 6771-6772.
32. (b) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
33. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082.
34. Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611-614.
35. For examples of Claisen related rearrangements on 2-bromocyclohexenol derivatives, see: (a) Hudlicky, T.; Oppong, K.; Duan, C.; Stanton, C.; Laufersweiler, M. J.; Natchus, M. G. Bioorg. Med. Chem. Lett. 2001, 11, 627-629.
36. (b) Jackson, R. W.; Shea, K. J. Tetrahedron Lett. 1994, 35, 1317-1320.
37. Felix, D.; Gschwend-Steen, K.; Wick, A. E.; Eschenmoser, A. Helv. Chim. Acta 1969, 52, 1031-1042.
38. Trost, B.; Belletire, J. L.; Godleski, S.; McDougal, P. G.; Balkovec, J. M.; Baldwin, J. J.; Christy, M. E.; Ponticello, G. S.; Varga, S. L.; Springer, J. P. J. Org. Chem. 1986, 51, 2370-2374.
39. Sustmann, R.; Hopp, P.; Holl, P. Tetrahedron Lett. 1989, 30, 689-692.
40. Mascareñas, J. L.; Pérez-Sestelo, J.; Castedo, L.; Mouriño, A. Tetrahedron Lett. 1991, 32, 2813-2816.
41. Perlman, K. L.; Swenson, R. E.; Paaren, H. E.; Schnoes, H. K.; DeLuca, H. F. Tetrahedron Lett. 1991, 32, 7663-7666.
42. 3 analogues with an intact D-ring, but a connection between positions 18 and 20, see: (a) Cornella, I.; Pérez-Sestelo, J.; Mouriño, A.; Sarandeses, L. A. J. Org. Chem. 2002, 67, 4707-4714.
43. (b) Varela, C.; Nilsson, K.; Torneiro, M.; Mouriño, A. Helv. Chim. Acta 2002, 85, 3251-3261.