Efficient and practical synthesis of the a-ring precursor of 19-nor-1α,25-dihydroxyvitamin D3 and its 13C-or 2H-labeled derivative

Organic Letters

Volumn 3, Issue 14, 2001, Pages 2205-2207

  Hanazawa, Takeshi ^a   Inamori, Hajime ^a   Masuda, Tomoko ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 (TERT BUTYLDIMETHYLSILYLOXY) 2 CYCLOHEXENONE; 5-(TERT-BUTYLDIMETHYLSILYLOXY)-2-CYCLOHEXENONE; CALCITRIOL; CARBON; CYCLOHEXANONE DERIVATIVE; DEUTERIUM; DRUG DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ISOTOPE LABELING; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CALCITRIOL; CARBON ISOTOPES; CATALYSIS; CYCLIZATION; CYCLOHEXANONES; DEUTERIUM; ISOTOPE LABELING; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035850290     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016052q     Document Type: Article

References (31)

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9. Paricalcitol: (a) Graul, A.; Leeson, P. A.; Castaner, J. Drugs Future 1998, 23, 602. Ro 65-2299: (b) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681. Other analogues: Mikami, K.; Osawa, A.; Isaka, A.; Sawa, E.; Shimizu, M.; Terada, M.; Kubodera, N.; Nakagawa, K.; Tsugawa, N.; Okano, T. Tetrahedron Lett. 1998, 39, 3359. Zhou, X.; Zhu, G.-D.; Van Haver, D.; Vandewalle, M.; De Clercq, P. J.; Verstuyf, A.; Bouillon, R. J. Med. Chem. 1999, 42, 3539. (e) Verstuyf, A.; Verlinden. L.; Van Baelen, H.; Sabbe, K.; D'hallewyn, C.; De Clercq, P. J.; Vandewalle, M.; Bouillon, R. J. Bone Miner. Res. 1998, 13, 549. (f) Kubodera, N.; Okano, T.; Nakagawa, K.; Ozono, K.; Mikami, K. Curr. Pharm. Design 2000, 6, 791.
10. Paricalcitol: (a) Graul, A.; Leeson, P. A.; Castaner, J. Drugs Future 1998, 23, 602. Ro 65-2299: (b) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681. Other analogues: Mikami, K.; Osawa, A.; Isaka, A.; Sawa, E.; Shimizu, M.; Terada, M.; Kubodera, N.; Nakagawa, K.; Tsugawa, N.; Okano, T. Tetrahedron Lett. 1998, 39, 3359. Zhou, X.; Zhu, G.-D.; Van Haver, D.; Vandewalle, M.; De Clercq, P. J.; Verstuyf, A.; Bouillon, R. J. Med. Chem. 1999, 42, 3539. (e) Verstuyf, A.; Verlinden. L.; Van Baelen, H.; Sabbe, K.; D'hallewyn, C.; De Clercq, P. J.; Vandewalle, M.; Bouillon, R. J. Bone Miner. Res. 1998, 13, 549. (f) Kubodera, N.; Okano, T.; Nakagawa, K.; Ozono, K.; Mikami, K. Curr. Pharm. Design 2000, 6, 791.
11. Paricalcitol: (a) Graul, A.; Leeson, P. A.; Castaner, J. Drugs Future 1998, 23, 602. Ro 65-2299: (b) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681. Other analogues: Mikami, K.; Osawa, A.; Isaka, A.; Sawa, E.; Shimizu, M.; Terada, M.; Kubodera, N.; Nakagawa, K.; Tsugawa, N.; Okano, T. Tetrahedron Lett. 1998, 39, 3359. Zhou, X.; Zhu, G.-D.; Van Haver, D.; Vandewalle, M.; De Clercq, P. J.; Verstuyf, A.; Bouillon, R. J. Med. Chem. 1999, 42, 3539. (e) Verstuyf, A.; Verlinden. L.; Van Baelen, H.; Sabbe, K.; D'hallewyn, C.; De Clercq, P. J.; Vandewalle, M.; Bouillon, R. J. Bone Miner. Res. 1998, 13, 549. (f) Kubodera, N.; Okano, T.; Nakagawa, K.; Ozono, K.; Mikami, K. Curr. Pharm. Design 2000, 6, 791.
12. 3 and its derivatives using 1, see refs 2b and 3b-e.
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16. (a) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Koiwa, M.; Hareau, G. P-J.; Morizono, D.; Sato, F. Tetrahedron Lett. 1999, 40, 4199. Hareau, G. P-J.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099. Hareau, G. P-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640. (e) Hareau, G.; Koiwa, M.; Hanazawa, T.; Sato, F. Tetrahedron Lett. 1999, 40, 7493. (f) Hareau, G. P. J.; Koiwa, M.; Sato, F. Tetrahedron Lett. 2000, 41, 2385. (g) Koiwa, M.; Hareau, P. J.; Sato, F. Tetrahedron Lett. 2000, 41, 2389. (h) Hanazawa, T.; Okamoto, S.; Sato, F. Tetrahedron Lett., in press.
17. (a) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Koiwa, M.; Hareau, G. P-J.; Morizono, D.; Sato, F. Tetrahedron Lett. 1999, 40, 4199. Hareau, G. P-J.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099. Hareau, G. P-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640. (e) Hareau, G.; Koiwa, M.; Hanazawa, T.; Sato, F. Tetrahedron Lett. 1999, 40, 7493. (f) Hareau, G. P. J.; Koiwa, M.; Sato, F. Tetrahedron Lett. 2000, 41, 2385. (g) Koiwa, M.; Hareau, P. J.; Sato, F. Tetrahedron Lett. 2000, 41, 2389. (h) Hanazawa, T.; Okamoto, S.; Sato, F. Tetrahedron Lett., in press.
18. (a) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Koiwa, M.; Hareau, G. P-J.; Morizono, D.; Sato, F. Tetrahedron Lett. 1999, 40, 4199. Hareau, G. P-J.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099. Hareau, G. P-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640. (e) Hareau, G.; Koiwa, M.; Hanazawa, T.; Sato, F. Tetrahedron Lett. 1999, 40, 7493. (f) Hareau, G. P. J.; Koiwa, M.; Sato, F. Tetrahedron Lett. 2000, 41, 2385. (g) Koiwa, M.; Hareau, P. J.; Sato, F. Tetrahedron Lett. 2000, 41, 2389. (h) Hanazawa, T.; Okamoto, S.; Sato, F. Tetrahedron Lett., in press.
19. (a) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Koiwa, M.; Hareau, G. P-J.; Morizono, D.; Sato, F. Tetrahedron Lett. 1999, 40, 4199. Hareau, G. P-J.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099. Hareau, G. P-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640. (e) Hareau, G.; Koiwa, M.; Hanazawa, T.; Sato, F. Tetrahedron Lett. 1999, 40, 7493. (f) Hareau, G. P. J.; Koiwa, M.; Sato, F. Tetrahedron Lett. 2000, 41, 2385. (g) Koiwa, M.; Hareau, P. J.; Sato, F. Tetrahedron Lett. 2000, 41, 2389. (h) Hanazawa, T.; Okamoto, S.; Sato, F. Tetrahedron Lett., in press.
20. (a) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Koiwa, M.; Hareau, G. P-J.; Morizono, D.; Sato, F. Tetrahedron Lett. 1999, 40, 4199. Hareau, G. P-J.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099. Hareau, G. P-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640. (e) Hareau, G.; Koiwa, M.; Hanazawa, T.; Sato, F. Tetrahedron Lett. 1999, 40, 7493. (f) Hareau, G. P. J.; Koiwa, M.; Sato, F. Tetrahedron Lett. 2000, 41, 2385. (g) Koiwa, M.; Hareau, P. J.; Sato, F. Tetrahedron Lett. 2000, 41, 2389. (h) Hanazawa, T.; Okamoto, S.; Sato, F. Tetrahedron Lett., in press.
21. (a) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Koiwa, M.; Hareau, G. P-J.; Morizono, D.; Sato, F. Tetrahedron Lett. 1999, 40, 4199. Hareau, G. P-J.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099. Hareau, G. P-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640. (e) Hareau, G.; Koiwa, M.; Hanazawa, T.; Sato, F. Tetrahedron Lett. 1999, 40, 7493. (f) Hareau, G. P. J.; Koiwa, M.; Sato, F. Tetrahedron Lett. 2000, 41, 2385. (g) Koiwa, M.; Hareau, P. J.; Sato, F. Tetrahedron Lett. 2000, 41, 2389. (h) Hanazawa, T.; Okamoto, S.; Sato, F. Tetrahedron Lett., in press.
22. (a) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Koiwa, M.; Hareau, G. P-J.; Morizono, D.; Sato, F. Tetrahedron Lett. 1999, 40, 4199. Hareau, G. P-J.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099. Hareau, G. P-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640. (e) Hareau, G.; Koiwa, M.; Hanazawa, T.; Sato, F. Tetrahedron Lett. 1999, 40, 7493. (f) Hareau, G. P. J.; Koiwa, M.; Sato, F. Tetrahedron Lett. 2000, 41, 2385. (g) Koiwa, M.; Hareau, P. J.; Sato, F. Tetrahedron Lett. 2000, 41, 2389. (h) Hanazawa, T.; Okamoto, S.; Sato, F. Tetrahedron Lett., in press.
23. (a) Hikichi, S.; Hareau, G. P.-J.; Sato, F. Tetrahedron Lett. 1997, 38, 8299. (b) Koiwa, M.; Hareau, G. P-J.; Morizono, D.; Sato, F. Tetrahedron Lett. 1999, 40, 4199. Hareau, G. P-J.; Hikichi, S.; Sato, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2099. Hareau, G. P-J.; Koiwa, M.; Hikichi, S.; Sato, F. J. Am. Chem. Soc. 1999, 121, 3640. (e) Hareau, G.; Koiwa, M.; Hanazawa, T.; Sato, F. Tetrahedron Lett. 1999, 40, 7493. (f) Hareau, G. P. J.; Koiwa, M.; Sato, F. Tetrahedron Lett. 2000, 41, 2385. (g) Koiwa, M.; Hareau, P. J.; Sato, F. Tetrahedron Lett. 2000, 41, 2389. (h) Hanazawa, T.; Okamoto, S.; Sato, F. Tetrahedron Lett., in press.
24. Recovery of 2 was 75%.
25. Phenol was coproduced in 30% yield.
26. 2H reagent, see: Oshima, M.; Yamazaki, H.; Shimizu, I.; Nisar, M.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 6280.
27. 2b,3b
28. The reduction of 6 to 1 with Red-Al was reported to proceed in 97% yield; see ref 3b.
29. Thus, 1 was obtained in 35% overall yield in 11 steps from ethyl 3-hydroxy-4-chlorobutyrate.
30. Purchased from Aldrich.
31. 2H-1 was determined to be >93% by GC/MS analysis.