Stereoisomers of Ieodoglucomides A and B: Synthesis and Evaluation of Anticancer Activity

Chada Raji Reddy; Enukonda Jithender; Ashita Singh; Ramesh Ummanni

doi:10.1055/s-0033-1340714

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(06): 822-827
DOI: 10.1055/s-0033-1340714

paper

Stereoisomers of Ieodoglucomides A and B: Synthesis and Evaluation of Anticancer Activity

Chada Raji Reddy*

^aDivision of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad – 500 007, India

,

Enukonda Jithender

^aDivision of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad – 500 007, India

,

Ashita Singh

^bCentre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad – 500 007, India Fax: +91(40)27160512 eMail: rajireddy@iict.res.in

,

Ramesh Ummanni*

^bCentre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad – 500 007, India Fax: +91(40)27160512 eMail: rajireddy@iict.res.in

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Abstract

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Abstract

Asymmetric total synthesis of α-isomers of ieodoglucomides A and B along with their C14-epimers has been achieved starting from d-glucose. The key reactions involved are α-glycosylation and Grubbs olefin cross-metathesis. These stereochemical analogues and their β-isomers (natural products) were screened for their effects on cytotoxicity against various cancer cell lines and it was found that a few analogues are active relative to the natural ieodoglucomides.

Key words

glycolipids - glycosylation - cross-metathesis - cytotoxicity - stereoisomer

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References and Notes

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