A short and convenient access to a trans-hydrindane unit from the anti-meso-acetylmethyldivinylcyclopentane via a radical pathway

Tetrahedron Letters

Volumn 47, Issue 16, 2006, Pages 2747-2750

  Chapelon, Anne Sophie ^a   Ollivier, Cyril ^a   Santelli, Maurice ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLMETHYLDIVINYLCYCLOPENTANE; ALPHA CARBONYL; ALPHA XANTHYL KETONE; CARBONYL DERIVATIVE; CYCLOPENTANE DERIVATIVE; HYDRINDANE; INDAN DERIVATIVE; UNCLASSIFIED DRUG; VITAMIN D DERIVATIVE; XANTHIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 33644990720     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.076     Document Type: Article

References (46)

1. E. Breitmaier Terpene 2005 VCH Verlagsgesellschaft Germany
2. T.L. Ho Carbocyclic Construction in Terpene Synthesis 1988 John Wiley & Sons
3. L.F. Fieser M. Fieser Steroids 3rd ed. 1959 Reinhold New York
4. C. Djerassi Steroid Reactions 1963 Holden-Day San Francisco
5. A.A. Akhrem Y.A. Titov Total Steroid Synthesis 1970 Plenum Press New York
6. R.T. Blickenstaff A.C. Ghoosh G.C. Wolf Total Steroid Synthesis 1974 Academic Press New York
7. D. Feldman F.H. Glorieux J.W. Pike Vitamin D 1997 New York Academic Press
8. A.W. Norman R. Bouillon M. Thomasset Vitamin D Endocrine System: Structural, Biological, Genetic and Clinical Aspects 2000 Vitamin D Workshop: University of California Riverside Riverside, CA
9. For reviews on various synthetic approaches to vitamin D and its analogs, see: R. Pardo, and M. Santelli Bull. Soc. Chim. Fr. 1985 98
10. H. Dai, and G.H. Posner Synthesis 1994 1383
11. G.-D. Zhu, and W.H. Okamura Chem. Rev. 95 1995 1877
12. G.H. Posner, and M. Kahraman Eur. J. Org. Chem. 2003 3889
13. F.J. Zeelen Medicinal Chemistry of Steroids 1990 Elsevier Amsterdam
14. R. Bouillon, W.H. Okamura, and A.W. Norman Endocr. Rev. 16 1995 200
15. M.J. Beckman, and H.F. DeLuca G.P. Ellis D.K. Luscombe A.W. Oxford Prog. Med. Chem. Vol. 35 1998 Elsevier Amsterdam 1
16. For a well-documented review on trans-hydrindane synthesis, see: P. Jankowski, S. Marczak, and J. Wicha Tetrahedron 54 1998 12071
17. R. Pardo, P. Archier, and M. Santelli Bull. Soc. Chim. Fr. 1986 760 765
18. H.L. Gordon, S. Freeman, and T. Hudlicky Synlett 2005 2911
19. N.L. Allinger, and M.T. Tribble Tetrahedron 28 1972 1191
20. B. Lo Cicero, F. Weisbuch, and G. Dana J. Org. Chem. 46 1981 914
21. G. Quinkert Experientia 13 1957 381
22. H.H. Inhoffen, G. Quinkert, S. Schutz, D. Dampe, and G.F. Domagk Chem. Ber. 90 1957 664
23. R. Rodriguez, C. Ollivier, and M. Santelli Tetrahedron Lett. 44 2004 2289
24. R. Rodriguez, C. Ollivier, and M. Santelli Synlett 2006 312
25. Gonzalès-Avión and Mouriño showed that different substituents at the C-12 position increased to 4.4 times the affinity of the related calcitriol analogs for the vitamin D receptor (VDR). X.C. Gonzalès-Avión, and A. Mouriño Org. Lett. 5 2003 2291
26. B. Lythgoe, D.A. Roberts, and I. Waterhouse J. Chem. Soc., Perkin Trans. 1 1977 2608
27. For isomerization problems reported in the literature, see: P.E. Peterson, and R.L. Breedlove Leffew J. Org. Chem. 51 1986 1948
28. A. Tubul, and M. Santelli Tetrahedron 44 1988 3975
29. H. Pellissier, R. Faure, and M. Santelli J. Chem. Soc., Chem. Commun. 1995 1847
30. N. Mariet, H. Pellissier, M. Ibrahim-Ouali, and M. Santelli Eur. J. Org. Chem. 2004 2679
31. Unpublished results: Reaction performed on multigram scale (0.8 mol of 7 ) gave 8 and 9 in 47% yield and with a 26:74 dl/meso ratio.
32. For reviews on the chemistry of xanthates, see: S.Z. Zard Angew. Chem., Int. Ed. 36 1997 672
33. B. Quiclet-Sire, and S.Z. Zard Phosphorus, Sulfur Silicon 153-154 1999 137
34. S.Z. Zard 1st ed. P. Renaud M. Sibi Radical in Organic Synthesis 2001 Wiley-VCH GmbH Weinheim, Germany
35. For examples of cyclization of an α-carbonyl radical generated from the corresponding xanthate, see: E. Bacqué, F. Pautrat, and S.Z. Zard Org. Lett. 5 2003 325
36. M.E. Briggs, M. El Qacemi, C. Kalaï, and S.Z. Zard Tetrahedron Lett. 45 2004 6017
37. P.R. Blakemore, P.J. Kocienski, S. Marzcak, and J. Wicha Synthesis 1999 1209
38. Both dl- and anti-meso-acetylmethyldivinylcyclopentanes 8 and 9 are particularly difficult to separate by liquid chromatography or distillation on multigram scale. These problems were already reported on small quantities: H. Pellissier, and M. Santelli Tetrahedron 52 1996 9093
39. Ester and malonate xanthate derivatives have been reported to be synthesized by reaction of their respective enolates with diethyl bisdithiocarbonate in 50-58% yield. V. Maslak, Ž. Čeković, and R.N. Saičić Synlett 1998 1435
40. D.L.J. Clive, and D.R. Cheshire J. Chem. Soc., Chem. Commun. 1987 1520
41. N.A. Porter, V.H.-T. Chang, D.R. Magnin, and B.T. Wright J. Am. Chem. Soc. 110 1988 3554
42. D.P. Curran, and C.-T. Chang J. Org. Chem. 54 1989 3140
43. J.L. Broeker, and K.N. Houk J. Org. Chem. 56 1991 3651
44. K. Mori, and Y. Nakamura J. Org. Chem. 34 1969 4170
45. J. Boivin, L. Ramos, and S.Z. Zard Tetrahedron Lett. 39 1998 6877
46. C.H. Chen J. Heterocycl. Chem. 13 1976 1079