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Issue 9, 2016
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Synthesis of the aglycon of aspafiliosides E and F based on cascade reactions

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Abstract

A synthesis of C17α-OH-tigogenin, the aglycon of aspafiliosides E and F, is described. The main features of the synthesis are three cascade processes, which involve the iodo-lactonization of furostan-26-acid to open ring E, a cascade hydrolysis/intramolecular SN2 process to close ring E, and a cascade intramolecular redox-ketalization process to close ring F. This synthesis would enrich the strategies used for the manipulation of spiroketals in steroidal sapogenins and other substrates.

Graphical abstract: Synthesis of the aglycon of aspafiliosides E and F based on cascade reactions

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Publication details

The article was received on 26 Oct 2015, accepted on 30 Nov 2015 and first published on 18 Dec 2015


Article type: Communication
DOI: 10.1039/C5CC08856A
Chem. Commun., 2016,52, 1942-1944

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    Synthesis of the aglycon of aspafiliosides E and F based on cascade reactions

    J. Wu, Y. Shi and W. Tian, Chem. Commun., 2016, 52, 1942
    DOI: 10.1039/C5CC08856A

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