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

Author:
Wu, Jing-Jing, Shi, Yong, Tian, Wei-Sheng
Source:
Chemical communications 2016 v.52 no.9 pp. 1942-1944
ISSN:
1364-548X
Subject:
hydrolysis, redox reactions, sapogenins, saponins, synthesis
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.
Agid:
6386364