Synthesis of (25R)-17α-Hydroxy-22-oxocholest-5-ene-3β,16β,26-triyl Triacetate: A One-Pot Approach to the Protected Aglycon Analogue of OSW-1

Title: Synthesis of (25R)-17α-Hydroxy-22-oxocholest-5-ene-3β,16β,26-triyl Triacetate: A One-Pot Approach to the Protected Aglycon Analogue of OSW-1

Volume: 8 Issue: 5

Author(s): Maria A. Fernandez-Herrera, Ma. G. Hernandez-Linares, Gabriel Guerrero-Luna, Socorro Meza-Reyesa, Sara Montiel-Smith and Jesus Sandoval-Ramirez

Affiliation:

Keywords: Acetolysis, extraction, OSW-1, pennogenin, sapogenin side chain, spirostan, saponins, cardiovascular, gastrointestinal, hydroxysapogenin

Abstract: The spirostanic side chain of pennogenin can be quantitatively transformed under mild acidic conditions in a 22-oxocholestanic framework through a one step procedure. This methodology is the shortest way to afford the 3,16,26- trihydroxy-22-oxocholestanic derivative, analogue of the protected aglycon of the potent antitumor agent OSW-1. The primary hydroxyl group at C-26 could be selectively transformed.

Cite this article as:

A. Fernandez-Herrera Maria, G. Hernandez-Linares Ma., Guerrero-Luna Gabriel, Meza-Reyesa Socorro, Montiel-Smith Sara and Sandoval-Ramirez Jesus, Synthesis of (25R)-17α-Hydroxy-22-oxocholest-5-ene-3β,16β,26-triyl Triacetate: A One-Pot Approach to the Protected Aglycon Analogue of OSW-1, Letters in Organic Chemistry 2011; 8 (5) . https://dx.doi.org/10.2174/157017811795685018