Stereoselective syntheses of unnatural steroidal C(20R) aldehydes by ionic hydrogenation of C-20 tertiary alcohols

Tetrahedron Letters

Volumn 47, Issue 52, 2006, Pages 9343-9347

  Shingate, Bapurao B ^a   Hazra, Braja G ^a   Pore, Vandana S ^a   Gonnade, Rajesh G ^a   Bhadbhade, Mohan M ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

1,3 Dithiane; Ionic hydrogenation; Oxidative hydrolysis; Stereoselective synthesis; Unnatural C 20 aldehydes

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE; PREGNENOLONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; HYDROGENATION; HYDROLYSIS; ISOMER; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33751175164     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.116     Document Type: Article

References (57)

1. Adam G., and Marquardt V. Phytochemistry 25 (1986) 1787-1799
2. Kinney W.A., Zhang X., Williams J.I., Johnston S., Michalak R.S., Deshpande M., Dostal L., and Rosazza J.P.N. Org. Lett. 2 (2000) 2921-2922
3. Yamamoto K., Takahashi J., Hamano K., Yamada S., Yamaguchi K., and Deluca H.F. J. Org. Chem. 58 (1993) 2530-2537
4. Yamamoto K., Shimizu M., Yamada S., Iwata S., and Hoshino O. J. Org. Chem. 58 (1993) 2530-2537
5. Deng S., Yu B., Lou Y., and Hui Y. J. Org. Chem. 64 (1999) 202-208
6. Nakanishi K. Pure Appl. Chem. 25 (1971) 167-195
7. Kovganko N.V., and Ananich S.K. Chem. Nat. Compd. 35 (1999) 229-259
8. Koreeda M., and Koizumi N. Tetrahedron Lett. 19 (1978) 1641-1644
9. Teicher B.A., Koizumi N., Koreeda M., Shikita M., and Talalay P. Eur. J. Biochem. 91 (1978) 11-19
10. Saito N., Suhara Y., Kurihara M., Fujishima T., Honzawa S., Takayanagi H., Kozono T., Matsumoto M., Ohmori M., Miyata N., Takayama H., and Kittaka A. J. Org. Chem. 69 (2004) 7463-7471
11. Vanderah D.J., and Djerassi C. Tetrahedron Lett. 8 (1977) 683-686
12. Vanderah D.J., and Djerassi C. J. Org. Chem. 43 (1978) 1442-1448
13. Yamamoto S., Watanabe B., Otsuki J., Nakagawa Y., Akamatsu M., and Miyagawa H. Bioorg. Med. Chem. 14 (2006) 1761-1770
14. Fujishima T., Konno K., Nakagawa K., Kurobe M., Okano T., and Takayama H. Bioorg. Med. Chem. 8 (2000) 123-134
15. Sicinski R.R., Rotkiewicz P., Kolinski A., Sicinski W., Prahl J.M., Smith C.M., and DeLuca H.F. J. Med. Chem. 45 (2002) 3366-3380
16. Blaehr L.K.A., Bjorkling F., Calverley M.J., Binderup E., and Begtrup M. J. Org. Chem. 68 (2003) 1367-1375
17. Binderup L., Latini S., Binderup E., Bretting C., Calverley M., and Hansen K. Biochem. Pharmacol. 42 (1991) 1569-1575
18. Posner G.H., and Kahraman M. Eur. J. Org. Chem. (2003) 3889-3895 and references cited therein
19. For construction of the steroidal side chain with unnatural configuration at C-20 see:. Tanabe M., and Hayashi K. J. Am. Chem. Soc. 102 (1980) 862-863
20. Midland M.M., and Kwon Y.C. Tetrahedron Lett. 23 (1982) 2077-2080
21. Schuff N.R., and Trost B.M. J. Org. Chem. 48 (1983) 1404-1412
22. Tahashi T., Ootake A., Tsuji J., and Tachibana K. Tetrahedron 41 (1985) 5747-5754
23. Mikami K., Kawamoto K., and Nakai T. Chem. Lett. (1985) 115-118
24. Koreeda M., and George I.A. J. Am. Chem. Soc. 108 (1986) 8098-8100
25. Ibuka T., Taga T., Shingu T., Saitao M., Nishii S., and Yamamoto Y. J. Org. Chem. 53 (1988) 3947-3952 and references cited therein
26. Harada S., Kiyono H., Nishio R., Taguchi T., and Hanzawa Y. J. Org. Chem. 62 (1997) 3994-4001 and references cited therein
27. Yu W., and Jin Z. J. Am. Chem. Soc. 124 (2002) 6576-6583
28. He Z., Yi C.S., and Donaldson W.A. Org. Lett. 5 (2003) 1567-1569
29. Watanabe B., Yamamoto S., Sasaki K., Nakagawa Y., and Miyagawa H. Tetrahedron Lett. 45 (2004) 2767-2769 and references cited therein
30. Shi B., Wu H., Yu B., and Wu J. Angew. Chem., Int. Ed. 43 (2004) 4324-4327
31. Shi B., Tang P., Hu X., Liu J.O., and Yu B. J. Org. Chem. 70 (2005) 10354-10367
32. Tsubuki M., Ohinata A., Tanaka T., Takahashi K., and Honda T. Tetrahedron 61 (2005) 1095-1100
33. Goto R., Morisaki M., and Ikekawa N. Chem. Pharm. Bull. 31 (1983) 3528-3533
34. Yamamoto K., Sun W.Y., Ohta M., Hamada K., Deluca H.F., and Yamada S. J. Med. Chem. 39 (1996) 2727-2737
35. Masuno H., Yamamoto K., Wang X., Choi M., Ooizumi H., Shinki T., and Yamada S. J. Med. Chem. 45 (2002) 1825-1834
36. Sato Y., Sonoda Y., and Saito H. Chem. Pharm. Bull. 28 (1980) 1150-1156
37. Sydykov Zh.S., and Segal G.M. Izv. Akad. Nauk SSSR, Ser. Khim. 11 (1976) 2581-2584
38. Sucrow W., and Nooy M.V. Liebigs Ann. Chem. (1982) 1897-1906
39. Liu X., Pan X., Li Y., and Liang X. Huaxue Xuebao 46 (1988) 561-566
40. Shingate B.B., Hazra B.G., Pore V.S., Gonnade R.G., and Bhadbhade M.M. Chem. Commun. (2004) 2194-2195
41. Hazra B.G., Basu S., Bahule B.B., Pore V.S., Vyas B.N., and Ramraj V.M. Tetrahedron 53 (1997) 4909-4920
42. Marino J.P., and Abe H. J. Am. Chem. Soc. 103 (1981) 2907-2909
43. Zheng Y., and Li Y. J. Org. Chem. 68 (2003) 1603-1606 and references cited therein
44. Gu Q., Zheng Y.-H., and Li Y.-C. Synthesis 6 (2006) 975-978
45. Mandai T., Matsumoto T., Kawada M., and Tsuji J. Tetrahedron 50 (1994) 475-486 and references cited therein
46. Kim J.-G., Cho D.H., and Jang D.O. Tetrahedron Lett. 45 (2004) 3031-3033
47. Lecomte V., Stephan E., and Jaouen G. Tetrahedron Lett. 46 (2005) 1123-1126
48. Khripach V., Litvinovskaya R., Baranovsky A., and Drach S. Tetrahedron Lett. 31 (1990) 7065-7068
49. Posner G.H., and Switzer C. J. Am. Chem. Soc. 108 (1986) 1239-1244
50. Peters R.H., Crowe D.F., Avery M.A., Chong W.K.M., and Tanabe M. J. Med. Chem. 32 (1989) 2306-2310
51. Tedesco R., Fiaschi R., and Napolitano E. J. Org. Chem. 60 (1995) 5316-5318
52. Carey F.A., and Tremper H.S. J. Am. Chem. Soc. 90 (1968) 2578-2583
53. Carey F.A., and Tremper H.S. J. Am. Chem. Soc. 91 (1969) 2967-2972
54. Magaraci F., Jimenz C.J., Rodrigues J.C.F., Braga M.V., Yardley V., Luca-Fradley K., Croft S.L., Souza W., Ruiz-Prez L.M., Urbina J., Pacanowska D.G., and Gilbert J.H. J. Med. Chem. 46 (2003) 4714-4727
55. 2: C, 67.33; H, 10.20; S, 11.59. Found: C, 67.22; H, 9.96; S, 11.33.
56. 2: C, 69.77; H, 9.54; S, 13.79. Found: C, 69.87; H, 9.52; S, 13.74.
57. -3. Crystallographic data (excluding structure factors) for the structure 21 in this letter has been deposited with the Cambridge Crystallographic Data Centre as Supplementary publication number CCDC 606459.