Synthesis of new steroid analogues by samarium diiodide induced cyclisations of γ-naphthyl 1,3-diones

Tetrahedron Asymmetry

Volumn 21, Issue 11-12, 2010, Pages 1601-1610

  Wefelscheid, Ulrike K ^a,b   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 [2 (6 METHOXY 1 NAPHTHYL)ETHYL] 2 METHYLCYCLOPENTANE 1,3 DIONE; 2 METHYL 2 [2 (1 NAPHTHYL)ETHYL]CYCLOHEXANE 1,3 DIONE; 2 METHYL 2 [2 (1-NAPHTHYL)ETHYL]CYCLOPENTANE 1,3 DIONE; ALUMINUM CHLORIDE; EQUILENIN; NAPHTHYL GROUP; PROTON; SAMARIUM DIIODIDE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; FRAGMENTATION REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 77956647738     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.04.036     Document Type: Article

References (58)

1. J.-L. Namy , and H.B. Kagan Nouv. J. Chim. 1 1977 5 7
2. P. Girard , J.-L. Namy , and H.B. Kagan J. Am. Chem. Soc. 102 1980 2693 2698
3. Selected reviews: D.J. Procter , R.A. Flowers II , and T. Skrydstrup Organic Synthesis using Samarium Diiodide 2010 The Royal Society of Chemistry Cambridge
4. K.C. Nicolaou , S.P. Ellery , and J.S. Chen Angew. Chem. 121 2009 7276 7301 Angew. Chem., Int. Ed. 2009, 48, 7140-7165
5. I.M. Rudkin , L.C. Miller , and D.J. Procter Organomet. Chem. 34 2008 19 45
6. K. Gopalaiah , and H.B. Kagan New J. Chem. 32 2008 607 637
7. J.-P. Ebran , C.M. Jensen , S.A. Johannesen , J. Karaffa , K.B. Lindsay , R. Taaning , and T. Skrydstrup Org. Biomol. Chem. 4 2006 3553 3564
8. M. Berndt , S. Gross , A. Hölemann , and H.-U. Reissig Synlett 2004 422 438
9. D.J. Edmonds , D. Johnston , and D.J. Procter Chem. Rev. 104 2004 3371 3403
10. J.M. Concellón , and H. Rodriguez-Solla Chem. Soc. Rev. 33 2004 599 609
11. H.B. Kagan Tetrahedron 59 2003 10351 10372
12. A. Krief , and A.-M. Laval Chem. Rev. 99 1999 745 777
13. G.A. Molander , and C.R. Harris Tetrahedron 54 1998 3321 3354
14. F.A. Khan , and R. Zimmer J. Prakt. Chem. 339 1997 101 104
15. G.A. Molander , and C.R. Harris Chem. Rev. 96 1996 307 338
16. C.U. Dinesh , and H.-U. Reissig Angew. Chem. 111 1999 874 876 Angew. Chem., Int. Ed. 1999, 38, 789-791
17. For related examples of ketyl-aryl couplings see: H.-G. Schmalz , S. Siegel , and J.W. Bats Angew. Chem. 107 1995 2597 2599 Angew. Chem., Int. Ed. 1995, 34, 2383-2385
18. C.-W. Kuo , and J.M. Fang Synth. Commun. 31 2001 877 892
19. N. Kise , T. Suzumoto , and T. Shono J. Org. Chem. 59 1994 1407 1413
20. R. Gorny , H.J. Schäfer , R. Fröhlich , and B. Wibbeling Eur. J. Org. Chem. 2003 2919 2932
21. U.K. Wefelscheid , M. Berndt , and H.-U. Reissig Eur. J. Org. Chem. 2008 3635 3646
22. M. Berndt , and H.-U. Reissig Synlett 2001 1290 1292
23. E. Nandanan , C.U. Dinesh , and H.-U. Reissig Tetrahedron 56 2000 4267 4277
24. R.S. Kumaran , I. Brüdgam , and H.-U. Reissig Synlett 2008 991 994
25. S. Gross , and H.-U. Reissig Synlett 2002 2027 2030
26. C. Beemelmanns , V. Blot , S. Gross , D. Lentz , and H.-U. Reissig Eur. J. Org. Chem. 2010 2716 2732
27. C. Beemelmanns , and H.-U. Reissig Org. Biomol. Chem. 7 2009 4475 4480
28. V. Blot , and H.-U. Reissig Eur. J. Org. Chem. 2006 4989 4992
29. V. Blot , and H.-U. Reissig Synlett 2006 2763 2766
30. S. Gross , and H.-U. Reissig Org. Lett. 5 2003 4305 4307
31. J.-S. Shiue , M.-H. Lin , and J.M. Fang J. Org. Chem. 62 1997 4643 4649
32. For electroreductive intramolecular coupling of 1-indolealkanones see: N. Kise , T. Mano , and T. Sakurai Org. Lett. 10 2008 4617 4620
33. F. Aulenta , U.K. Wefelscheid , and H.-U. Reissig Eur. J. Org. Chem. 2008 2325 2335
34. F. Aulenta , M. Berndt , I. Brüdgam , H. Hartl , S. Sörgel , and H.-U. Reissig Chem. Eur. J. 13 2007 6047 6062
35. M. Berndt , I. Hlobilová , and H.-U. Reissig Org. Lett. 6 2004 957 960
36. U.K. Wefelscheid , and H.-U. Reissig Adv. Synth. Catal. 350 2008 65 69
37. M. Sakakibara , and A. Ogawa Tetrahedron Lett. 35 1994 8013 8014
38. P.P. Fu , and R.G. Harvey Chem. Rev. 78 1978 317 361
39. M. Kimura , Y. Horino , R. Mukai , S. Tanaka , and Y. Tamaru J. Am. Chem. Soc. 123 2001 10401 10402
40. H. Ohno , M. Okumura , S.-I. Maeda , H. Iwasaki , R. Wakayama , and T. Tanaka J. Org. Chem. 68 2003 7722 7732
41. H. Ohno , R. Wakayama , S.-I. Maeda , H. Iwasaki , M. Okumura , C. Iwata , H. Mikamiyama , and T. Tanaka J. Org. Chem. 68 2003 5909 5916
42. H. Ohno , S.-I. Maeda , M. Okumura , R. Wakayama , and T. Tanaka Chem. Commun. 2002 316 317
43. Wefelscheid, U. K. Dissertation, Freie Universität Berlin, 2007.
44. Crystallographic data for cis-8: U.K. Wefelscheid , I. Brüdgam , H. Hartl , and H.-U. Reissig Z. Kristallogr. - New Cryst. Struct. 222 2007 467 468 For trans-8: CCDC 659638, the data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif
45. 13C NMR data of cis- and trans-fused 6/6-ring systems, see: B. Frey , J. Schnaubelt , and H.-U. Reissig Eur. J. Org. Chem. 1999 1377 1384
46. Review: R.A. Flowers II Synlett 2008 1427 1439
47. P.R. Chopade , E. Prasad , and R.A. Flowers II J. Am. Chem. Soc. 126 2004 44 45
48. A.R. Daniewski , and T. Kowalczyk-Przewloka Tetrahedron Lett. 23 1982 2411 2414
49. Reviews dealing with synthetic applications of dearomatising processes: for reductive dearomatisations see: L.N. Mander Synlett 1991 134 144
50. T.J. Donohoe , R. Garg , and C.A. Stevenson Tetrahedron: Asymmetry 7 1996 317 344
51. A. Schultz Chem. Commun. 1999 1263 1271
52. For nucleophilic dearomatisations see: J. Clayden , and M.N. Kenworthy Synthesis 2004 1721 1736
53. F. López-Ortiz , M.J. Iglesias , I. Fernández , C.M.A. Sánchez , and G.R. Gómez Chem. Rev. 107 2007 1580 1691
54. G. Barbe , G. Pelletier , and A.B. Charette Org. Lett. 11 2009 3398 3401
55. For transition metal mediated dearomatisations see: T. Bach Angew. Chem. 108 1996 795 796 Angew. Chem., Int. Ed. 1996, 35, 729-730
56. A.R. Pape , K.P. Kaliappan , and E.P. Kündig Chem. Rev. 100 2000 2917 2940
57. For oxidative dearomatisations see: S. Quideau , L. Pouységu , and D. Deffieux Synlett 2008 467 495 and references cited therein
58. G. Haffer , U. Eder , G. Sauer , and R. Wiechert Chem. Ber. 108 1975 2665 2672