Side-chain opening of steroidal sapogenins to form 22-oxocholestanic skeletons. An approach to analogues of the aglycone of the potent anticancer agent OSW-1

Authors

  • María A. Fernández-Herrera Benemérita Universidad Autónoma de Puebla
  • Jesús Sandoval-Ramírez Benemérita Universidad Autónoma de Puebla
  • Socorro Meza-Reyes Benemérita Universidad Autónoma de Puebla
  • Sara Montiel-Smith Benemérita Universidad Autónoma de Puebla

DOI:

https://doi.org/10.29356/jmcs.v53i3.993

Keywords:

steroidal sapogenins, acetolysis, aglycone, OSW-1

Abstract

The side-chain opening of 25R and 25S steroidal sapogenins to form 22-oxocholestanic skeletons is described. The transformation was produced under mild conditions providing high yields (70-87%), in a one pot procedure (some acetylated starting material is recovered). This methodology yields 17-deoxy-26-oxy analogues of the aglycone of the potent anticancer agent OSW-1. All products were fully characterized by 1D and 2D NMR; the most representative displacements are briefly discussed.

 

 

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Author Biographies

María A. Fernández-Herrera, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

Jesús Sandoval-Ramírez, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

Socorro Meza-Reyes, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

Sara Montiel-Smith, Benemérita Universidad Autónoma de Puebla

Facultad de Ciencias Químicas

References

1. Hostettmann, K.; Marston, A. Saponins; Cambridge University Press, New York, 1995, 76-96.
2. (a) Marker, R. E.; Rohrmann, E. J. Am. Chem. Soc. 1939, 61, 3592-3593. (b) Marker, R. E.; Krueger, J. J. Am. Chem. Soc. 1940, 62, 3349-3350. (c) Marker, R. E.; Tsukamoto, T.; Turner, D. L. J. Am. Chem. Soc. 1940, 62, 2525-2532. (d) Marker, R. E. J. Am. Chem. Soc. 1940, 62, 3350-3352.
3. (a) Djerassi, C.; Ringold, H. J.; Rosenkranz, G. J. Am. Chem. Soc. 1951, 73, 5513-5514. (b) Kongkathip, N.; Kongkathip, B.; Noimai, N. Synth. Commun. 2006, 36, 865-874.
4. Kubo, S.; Mimaki, Y.; Terao, M.; Sashida, Y.; Nikaido, T.; Ohmoto, T. Phytochemistry 1992, 31, 3969-3973.
5. (a) Leamon, C. P.; Reddy, J. A.; Vlahov, I. R.; Vetzel, M.; Parker, N.; Nicoson, J. S.; Xu, L. C.; Westrick, E. Bioconjugate Chem. 2005, 16, 803-811. (b) Gehrmann, M. L.; Fenselau, C.; Hathout, Y. J. Proteome Res. 2004, 3, 403-409. (c) Criado, J. J.; Fernández, E. R.; Manzano, J. L.; Alonso, A.; Barrena, S.; Medarde, M.; Pelaez, R.; Tabernero, M. D.; Orfao, A. Bioconjugate Chem. 2005, 16, 275-282. (d) Crow, D. M.; Williams, L.; Colcher, D.; Wong, J. Y. C.; Raubitschek, A.; Shively, J. E. Bioconjugate Chem. 2005, 16, 1117-1125.
6. (a) Deng, S.; Yu, B.; Lou, Y.; Hui, Y. J. Org. Chem. 1999, 64, 202208. (b) Yoichi, Y. Farumashia 2001, 37, 1044-1045. (c) Yu, W.; Jin, Z. J. Am. Chem. Soc. 2002, 124, 6576-6583. (d) Morzycki, J. W.; Wojtkielewicz, A. Carbohydr. Res. 2002, 337, 1269-1274.
7. Dewick, P. M. Medicinal Natural Products. A Biosynthetic Approach. 2nd Ed. John Wiley & Sons, Chichester. 2002, 237239.
8. Djerassi, C.; Halpern, O.; Pettit, G. R.; Thomas, G. H. J. Org. Chem. 1959, 24, 1-6.
9. Tian, W. S.; Guan, H. P.; Pan, X. F. Chin. J. Chem. 2003, 21, 794798.
10. (a) Sandoval-Ramírez, J.; Castro-Méndez, A.; Meza-Reyes, S.; Reyes-Vázquez, F.; Santillán, R.; Farfán, N. Tetrahedron Lett. 1999, 40, 5143-5146. (b) Sandoval-Ramírez, J.; Meza-Reyes, S.; del Rio, R. E.; Hernández-Linares, G.; Suárez-Rojas, A.; Rincón, S.; Farfán, N.; Santillán, R. L. Steroids 2003, 68, 199-204. (c) Rincón, S.; del Río, R. E.; Sandoval-Ramírez, J.; Meza-Reyes, S.; Montiel-Smith, S.; Fernández, M. A.; Farfán, N.; Santillán, R. Tetrahedron 2006, 62, 2594-2602. (d) Hernández-Linares, G.; Meza-Reyes, S.; Montiel-Smith, S.; Sandoval-Ramírez, J.; Gómez-Calvario, V.; Bernès, S. J. Mex. Chem. Soc. 2007, 51, 217-221.

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Published

2019-06-24

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