Regioselective cleavage of 22-oxo-23-spiroketals. Novel cholestanic frameworks with pyranone and cyclopentenone E rings on the side chain

Steroids
Yliana LópezRosa Santillan

Abstract

The regioselective opening of the F ring of 22-oxo-23-spiroketals using a saturated solution of HCl in acetic anhydride yielded novel cholestanic frameworks with pyranone or cyclopentenone E rings. The structures of the new derivatives of sarsasapogenin, diosgenin and hecogenin thus obtained were established using one and two dimensional (1)H, (13)C experiments (DEPT, COSY, HETCOR, HMBC, ROESY, and NOESY). The X-ray analysis for compound 11b confirmed the 23R configuration for the new stereogenic center.

References

Oct 2, 2002·The Journal of Organic Chemistry·Romana Anulewicz-OstrowskaJacek Wójcik
Feb 28, 2003·Steroids·Jesús Sandoval-RamírezRosa Luisa Santillan
May 18, 2005·Steroids·Zhong-Xing JiangYing-Sheng Zhao
Oct 4, 2005·Steroids·Yliana LópezNorberto Farfán
Nov 6, 2007·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·Linda Saxe EinbondFredi Kronenberg
Feb 5, 2008·Steroids·Yliana LópezJacek W Morzycki
Nov 11, 2008·Steroids·Mariana Macías-AlonsoMartín A Iglesias-Arteaga
May 26, 2009·Steroids·Izabella JastrzebskaJacek W Morzycki
Jul 27, 2010·Steroids·José Oscar H Pérez-DíazRosa Santillan
Dec 21, 2010·Steroids·Mariana Macias-AlonsoMartin A Iglesias-Arteaga

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Citations

Feb 1, 2014·Fitoterapia·Hai-Yan ShenWen-Li Mei

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