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

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

Journal Name: Letters in Organic Chemistry

Volume 8 , Issue 5 , 2011

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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.

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

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Article Details

VOLUME: 8
ISSUE: 5
Year: 2011
Page: [341 - 346]
Pages: 6
DOI: 10.2174/157017811795685018
Price: $58

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