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 | Zendy

María A. FernándezHerrera | Zendy; Jesús SandovalRamírez | Zendy; Socorro MezaReyes | Zendy; Sara MontielSmith | Zendy

Open 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

Author(s) -

María A. FernándezHerrera,

Jesús SandovalRamírez,

Socorro MezaReyes,

Sara MontielSmith

Publication year - 2019

Publication title -

journal of the mexican chemical society

Language(s) - English

Resource type - Journals

ISSN - 2594-0317

DOI - 10.29356/jmcs.v53i3.993

Subject(s) - sapogenin , aglycone , side chain , chemistry , stereochemistry , transformation (genetics) , combinatorial chemistry , organic chemistry , biochemistry , glycoside , polymer , gene , medicine , alternative medicine , pathology

The side-chain opening of 25R and 25S steroidal sapoge- nins to form 22-oxocholestanic skeletons is described. The transfor- mation 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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