Lewis acid-mediated isomerisation of (25R)-3β-acetoxy-5α-spirostan-23-one, a C-22 spiroacetal: an approach to the synthesis of C-23 spiroacetal steroidal sapogenins

descriptionPublicationkeyboard_double_arrow_right Article 01 Jan 1992 Spain English Publisher:Royal Society of Chemistry (RSC)Journal:J. Chem. Soc., Chem. Commun., volume 0, pages 275-277 (issn: 0022-4936,

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Authors: Hernández, Rosendo; Marrero-Tellado, José Juan; Prout, Keith; Suárez, Ernesto;

doi: 10.1039/c39920000275

handle: 10261/17577

Lewis acid-mediated isomerisation of (25R)-3β-acetoxy-5α-spirostan-23-one, a C-22 spiroacetal: an approach to the synthesis of C-23 spiroacetal steroidal sapogenins

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Abstract

This work was supported by the Investigation Programme No. PB0406 of the Dirección General de Investigación Científica y Técnica. J.J.M. thanks the Ministerio de Educación y Ciencia of Spain for a postdoctoral fellowship.

Treatment of (25R)-3β-acetoxy-5α-spirostan-23-one (23-oxo-tigogenin acetate)3 with titanium tetrachloride afforded the 22-oxo-23-spiroacetal isomer 4 in excellent yield.

3 pages, 1 figure, 2 schemes.

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Spain

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Spanish National Research Council
Spain

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