Application of the solid-phase Julia-Lythgoe olefination in vitamin D side-chain construction

Molecules

Volumn 11, Issue 8, 2006, Pages 655-660

  D'herde, Jo N ^a   De Clercq, Pierre J ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Julia Lythgoe olefination; Solid phase synthesis; Vitamin D

Indexed keywords

ALKENE; CARBON; VITAMIN D;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; SYNTHESIS;

ALKENES; CARBON; MODELS, CHEMICAL; VITAMIN D;

EID: 33748419954     PISSN: 14203049     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/11080655     Document Type: Article

References (23)

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.; Pike, J. W., Eds.; Academic Press: San Diego, 1997.
3. (a) Zhu, G.-D.; Okamura, W. H. Chem. Rev. 1995, 95, 1877-1952;
4. (b) Dai, H.; Posner, G. H. Synthesis 1994, 1383-1398.
5. (a) Nagpal, S.; Na, S.; Rathnachalam, R. Endocr. Rev. 2005, 26, 662-687;
6. (b) Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocr. Rev. 1995, 16, 200-257.
7. (a) Kabat, M. M.; Radinov, R. Curr. Opin. Drug Disc. 2001, 4, 808-833;
8. (b) Posner, G. H.; Kahraman, M. Eur. J. Org. Chem. 2000, 3889-3895.
9. (a) Cano, M.; Balasubramanian, S. Drug Future 2003, 28, 659-678;
10. (b) Ganesan, A. Drug Discov. Today 2002, 7, 47-55;
11. (c) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. 1996, 35, 17-42.
12. (a) Hijikuro, I.; Doi, T.; Takahashi, T. J. Am. Chem. Soc. 2001, 123, 3716-3722;
13. (b) Doi, T.; Hijikuro, I.; Takahashi, T. J. Am. Chem. Soc. 1999, 121, 6749-6750.
14. (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;
15. (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.
16. (a) Franzen, R. G. Tetrahedron 2000, 56, 685-691;
17. (b) Schlosser, M. Angew. Chem., Int. Ed. 1974, 13, 701-706.
18. D'herde, J. N. P.; De Clercq, P. J. Tetrahedron Lett. 2003, 44, 6657-6659.
19. Fréchet, J. M. J.; de Smet, M. D.; Farrell, M. J. Polymer 1979, 20, 675-680.
20. (a) Fernández, B.; Martinez Pérez, J. A.; Granja, J. R.; Castedo, L.; Mouriño, A. J. Org. Chem. 1992, 57, 3173-3178;
21. (b) Mascareñas, J. L.; Mouriño, A.; Castedo, L. J. Org. Chem. 1986, 51, 1269-1272.
22. Shabangi, M.; Sealy, J. M.; Fuchs, J. R.; Flowers II, R. A. Tetrahedron Lett. 1998, 39, 4429-4432.
23. In the compound chemical name of 4 and 5 the phenylsulfonyl group, although further connected via the 4-position to the solid phase (see Scheme 1), is named as such. The ACD/I-Lab Web service (ACD/IUPAC Name Free 8.05) was used to generate the core of the chemical names.