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2019•Journal of the Mexican Chemical SocietyOpen access

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

María A. Fernández‐Herrera, Jesús Sandoval-Ramı́rez, Socorro Meza‐Reyes, Sara Montiel‐Smith

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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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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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Available 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.

Key concepts: Sapogenin, Aglycone, Side chain, Chemistry, Stereochemistry, Transformation (genetics), Combinatorial chemistry, Organic chemistry

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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 — Research Paper | ScholarLens