Novel transformation of 23-bromosapogenins. Synthesis of (22S,23R)-22-hydroxy-23,26-epoxyfurostanes

doi:10.1016/S0040-4039(01)01165-0

Tetrahedron Letters

Volume 42, Issue 34, 20 August 2001, Pages 5989-5991

https://doi.org/10.1016/S0040-4039(01)01165-0 Get rights and content

Abstract

(22S,23S)-23-Bromosapogenins undergo rearrangement to the (22S,23R)-22-hydroxy-23,26-epoxyfurostanes during alkaline hydrolysis. An efficient degradation procedure of sarsapogenin via the corresponding bisfuran to the C₂₂ lactone is described.

(22S,23S)-23-Bromosapogenins undergo rearrangement to the (22S,23R)-22-hydroxy-23,26-epoxyfurostanes during alkaline hydrolysis.

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Acknowledgments

The work was financially supported by the Polish Ministry of Education within the project BST-124. X-Ray analysis was performed by Dr. R. Anulewicz-Ostrowska from the University of Warsaw. I.J. thanks the University of Warsaw for the fellowship.

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^†: Formerly: University of Warsaw, Bialystok Branch.

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Novel transformation of 23-bromosapogenins. Synthesis of (22S,23R)-22-hydroxy-23,26-epoxyfurostanes

Abstract

Section snippets

Acknowledgments

J. Chem. Soc. (C)

J. Am. Chem. Soc.

J. Am. Chem. Soc.

Tetrahedron Lett.

Eur. J. Med. Chem.