Efficient convergent synthesis of 1α,25-dihydroxyvitamin D 43 and its analogues by suzuki-miyaura coupling

Organic Letters

Volumn 5, Issue 4, 2003, Pages 523-525

  Hanazawa, Takeshi ^a   Koyama, Akiko ^a   Wada, Takeshi ^a   Morishige, Eiko ^a   Okamoto, Sentaro ^a   Sato, Fumie ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,7 ENYNE; ALKYNE DERIVATIVE; BORONIC ACID DERIVATIVE; CALCITRIOL; RETIFEROL; TITANIUM; UNCLASSIFIED DRUG; ALKYNE; BORANE DERIVATIVE; BORON TRIFLUORIDE; DRUG DERIVATIVE; EPICHLOROHYDRIN; LITHIUM DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SUZUKI MIYAURI COUPLING; CHEMISTRY; SYNTHESIS;

ALKYNES; BORANES; CALCITRIOL; CYCLIZATION; EPICHLOROHYDRIN; LITHIUM COMPOUNDS;

EID: 0038683611     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0274007     Document Type: Article

References (22)

1. Vitamin D; Feldman, D., Glorieux, F. H., Pike, J. W., Eds.; Academic Press: New York, 1997. Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200.
2. Vitamin D; Feldman, D., Glorieux, F. H., Pike, J. W., Eds.; Academic Press: New York, 1997. Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200.
3. Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877.
4. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
5. Hanazawa, T.; Wada, T.; Masuda, T.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 3975.
6. Tazumi, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1994, 1903.
7. Urabe, H.; Sato, F. Tetrahedron Lett. 1998, 39, 7329.
8. García, A. M.; Mascareñas, J. L.; Castedo, L.; Mouriño, A. J. Org. Chem. 1997, 62, 6353.
9. (a) Trost, B. M.; Dumas, J.; Villa, M. J. Am. Chem. Soc. 1992, 114, 9836.
10. (b) Trost, B. M.; Hanson, P. R. Tetrahedron Lett. 1994, 35, 8119.
11. Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. J. Org. Chem. 1986, 51, 3098 and references therein.
12. Vrielynck, S.; Vandewalle, M. Tetrahedron Lett. 1995, 36, 9023.
13. Subburaj, K.; Okamoto, S.; Sato, F. J. Org. Chem. 2002, 67, 1024.
14. 4/2 i-PrMgCl reagent: Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759. Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354.
15. 4/2 i-PrMgCl reagent: Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759. Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354.
16. 4/2 i-PrMgCl reagent: Sato, F.; Urabe, H.; Okamoto, S. Chem. Rev. 2000, 100, 2835. Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759. Sato, F.; Urabe, H. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 319-354.
17. (a) Kutner, A.; Zhao, H.; Fitak, H.; Wilson, S. R. Bioorg. Chem. 1995, 23, 22.
18. (b) Wirz, B.; Iding, H.; Hilpert, H. Tetrahedron: Asymmetry 2000, 11, 4171.
19. (c) Hilpert, H.; Wirz, B. Tetrahedron 2001, 57, 681.
20. (d) U.S. Patent 5,969,190, 1998.
21. (e) U.S. Patent 6,184,422, 1999.
22. 3 analogues by the Trost method was not reported.