Unusual oxidative transformations of a steroidal 16α,17α,22-triol

Steroids

Volumn 75, Issue 1, 2010, Pages 70-76

  Morzycki, Jacek W ^a   Pérez Díaz, José Oscar H ^a   Santillan, Rosa ^b   Wojtkielewicz, Agnieszka ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

^b DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

Autoxidation; Mitsunobu reaction; PDC oxidation; Swern oxidation

Indexed keywords

16ALPHA,17ALPHA DIHYDROXY 22 O TES ETHER; 6ALPHA,17ALPHA,22 TRIOL; ALDEHYDE; DIMETHYL SULFOXIDE; KETONE DERIVATIVE; SODIUM HYDROXIDE; STEROID; UNCLASSIFIED DRUG;

ARTICLE; AUTOOXIDATION; CHEMICAL STRUCTURE; MITSUNOBU REACTION; STEROID METABOLISM; SWERN OXIDATION;

CHOLESTENONES; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; SAPONINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; STEROIDS;

EID: 71849108499     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2009.10.002     Document Type: Article

References (24)

1. Morzycki J.W., and Wojtkielewicz A. Synthesis of a highly potent antitumor saponin OSW-1 and its analogues. Phytochem Rev 4 (2005) 259-277
2. Wojtkielewicz A., Długosz M., Maj J., Morzycki J.W., Nowakowski M., Renkiewicz J., et al. New analogues of the potent cytotoxic saponin OSW-1. J Med Chem 50 (2007) 3667-3673
3. Kruszewska A., Wilczewska A.Z., Wojtkielewicz A., and Morzycki J.W. Synthesis of 23-oxa-22-deoxo analogues of OSW-1 aglycone. Polish J Chem 80 (2006) 611-615
4. Morzycki JW, Wojtkielewicz A, Oklestkova J, Strnad M. Analogi saponiny OSW-1 o uproszczonej budowie. Polish Patent Application P 387235, February 9th, 2009.
5. Reich H.J., and Rigby J.H. Handbook of reagents for organic synthesis, vol. 3 (1999), John Wiley & Sons, Chichester, UK p. 340-342
6. Wang X., Zhang B., and Wang D.Z. Reductive and transition-metal-free oxidation of secondary alcohols by sodium hydride. J Am Chem Soc (2009) 10.1021/ja904224y
7. Ibuka T., Taga T., Shingu T., Saito M., Nishii S., and Yamamoto Y. New stereoselective synthesis of 20S and 20R steroidal side chains. Remarkable stereoselectivity differences between saturated and α,β unsaturated steroidal esters. J Org Chem 53 (1988) 3947-3952
8. Deng S., Yu B., Lou Y., and Hui Y. First total synthesis of an exceptionally potent antitumor saponin. OSW-1. J Org Chem 64 (1999) 202-208
9. Schmidt U., and Gleich P. Total synthesis of ulicyclamide. Angew Chem Int Ed 24 (1985) 569-571
10. Burla M.C., Caliandro R., Camalli M., Carrozzini B., Cascarano G.L., De Caro L., et al. SIR 2004: an improved tool for crystal structure determination and refinement. J Appl Cryst 38 (2005) 381-388
11. Sheldrick G.M. SHELXL-97. A program for the refinement of crystal structure (1997), University of Göttingen, Germany
12. Guo C., and Fuchs P.L. The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1. Tetrahedron Lett 39 (1998) 1099-1102
13. Chen L., Xu Q., Huang H., Lin J., and Tian W. Synthesis of 5(6)-dihydro-OSW-1 by using the intact skeleton of tigogenin. Tetrahedron Lett 48 (2007) 3475-3477
14. Xue J., Liu P., Pan Y., and Guo Z. A total synthesis of OSW-1. J Org Chem 73 (2008) 157-161
15. Madsen R. In: Fraser-Reid B., Tatsuta K., and Thiem J. (Eds). Glycoscience, chemistry and chemical biology, vol. 1, Chapter 2.2, Oxidation and reduction (2001), Springer p. 195-230
16. Perlin A.S. In: Horton D. (Ed). Advances in carbohydrate chemistry and biochemistry, vol. 60, glycal-cleavage oxidation (2006), Academic Press p. 184-250
17. Tidwell T.T. Oxidation of alcohols to carbonyl compounds via alkoxysulfonium ylides: the Moffatt, Swern and related reactions. Org React 39 (1990) 297-572
18. 4. J Org Chem 72 (2007) 2906-2916
19. Luche J.L. Lanthanides in organic chemistry. 1. Selective 1,2 reductions of conjugated ketones. J Am Chem Soc 100 (1978) 2226-2227
20. Mitsunobu O., and Yamada Y. Preparation of esters of carboxylic and phosphoric acid via quaternary phosphonium salts. Bull Chem Soc Jpn 40 (1967) 2380-2382
21. Mitsunobu O. The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis (1981) 1-28
22. Hughes D.L. The Mitsunobu reaction. Org React 42 (1992) 335-656
23. 31P NMR study. Aust J Chem 35 (1982) 767-774
24. HyperChem for Windows, Release 7.5, from Hypercube, Inc.; minimizations employed the MM+ force field and the Polak-Ribiere algorithm with RMS gradient 0.001 kcal/Å mol.