Abstract

FERNANDEZ-HERRERA, María A.; SANDOVAL-RAMIREZ, Jesús; MEZA-REYES, Socorro  and  MONTIEL-SMITH, Sara. 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. J. Mex. Chem. Soc [online]. 2009, vol.53, n.3, pp.126-130. ISSN 1870-249X.

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.

Keywords : steroidal sapogenins; acetolysis; aglycone; OSW-1.

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