Facile construction of the 7,8-olefin linkage in vitamin D3: A practical synthesis benefiting the vitamin D3 analog study

Synthetic Communications

Volumn 36, Issue 8, 2006, Pages 1141-1146

  Ono, Yoshiyuki ^a   Kashiwagi, Hirotaka ^a   Takahashi, Tadakatsu ^a  

^a CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

Horner Wittig olefination; Vitamin D3; Vitamin D3 analog

Indexed keywords

3BETA TERT BUTYLDIMETHYLSILYL 1ALPHA TERT BUTYLDIMETHYLSILYLOXY 2 METHYLENE 25 TRIMETHYLSILYLOXY 19 NORCOLECALCIFEROL; 3BETA TERT BUTYLDIMETHYLSILYL 1ALPHA TERT BUTYLDIMETHYLSILYLOXY 22 OXA 25 TRIMETHYLSILYLOXYVCOLECALCIFEROL; 3BETA TERT BUTYLDIMETHYLSILYL 1ALPHA TERT BUTYLDIMETHYLSILYLOXY 24,25,26 TRIHOMO 22 OXA 25 TRIMETHYLSILYLOXYCOLECALCIFEROL; 3BETA TERT BUTYLDIMETHYLSILYL 1ALPHA TERT BUTYLDIMETHYLSILYLOXY 25 TRIMETHYLSILYLOXY 19 NORCOLECALCIFEROL; 3BETA TERT BUTYLDIMETHYLSILYL 1ALPHA TERT BUTYLDIMETHYLSILYLOXY 25 TRIMETHYLSILYLOXYVCOLECALCIFEROL; ALKENE DERIVATIVE; COLECALCIFEROL; COLECALCIFEROL DERIVATIVE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; DRUG SYNTHESIS; HEATING; OLEFINATION; REACTION ANALYSIS;

EID: 33645001164     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500503645     Document Type: Article

References (13)

1. Bouillon, R.; Okamura, W. H.; Norman, A. W. Structure-function relationships in the vitamin D endocrine system. Endocr. Rev. 1995, 16, 200-257.
2. Kubodera, N. Development of OCT and ED-71. In Vitamin D; 2nd ed.; Elsiever Academic Press: San Diego, 2005; Vol. 2, pp. 1525-1542.
3. 3 selectively induces bone formation. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 13487-13491.
4. Slatopolsky, E.; Finch, J.; Brown, A. New vitamin D analogs. Kidney Int., Suppl. 2003, 85-87.
5. Fogh, K.; Kragballe, K. New vitamin D analogs in psoriasis. Curr. Drug Targets: Inflammation Allergy 2004, 3, 199-204.
6. 3 analogs substituted at the 2β-position and their preventive effects on bone mineral loss in ovariectomized rats. Chem. Pharm. Bull. (Tokyo) 1997, 45, 1626-1630.
7. 3 compounds of high biological activity: Synthesis and biological evaluation of 2-hydroxymethyl, 2-methyl, and 2-methylene analogs. J. Med. Chem. 1998, 41, 4662-4674.
8. Baggiolini, E. G.; Iacobelli, J. A.; Hennessy, B. M.; Batcho, A. D.; Sereno, J. F.; Uskokovic, M. R. Stereocontrolled total synthesis of 1α,25-dihydroxycholecalciferol and 1α,25-dihydroxyergocalciferol. J. Org. Chem. 1986, 51, 3098-3108.
9. Zhu, G.-D.; Okamura, W. H. Synthesis of vitamin D (calciferol). Chem. Rev. 1995, 95, 1877-1952.
10. 3 homologs. J. Med. Chem. 1992, 35, 3280-287.
11. 3 analogues. Chem. Pharm. Bull. (Tokyo) 1986, 34, 4410-4413.
12. 3 analogs: A novel class of potent regulators of cell growth and immune responses. Biochem. Pharmacol. 1991, 42, 1569-1575.
13. Perlman, K. L.; Swenson, R. E.; Paarena, H. E.; Schnoes, H. K.; DeLuca, H. F. Novel synthesis of 19-nor-vitamin D compounds. Tetrahedron Lett. 1991, 32, 7663-7666.