Synthesis 2014; 46(06): 822-827
DOI: 10.1055/s-0033-1340714
paper
© Georg Thieme Verlag Stuttgart · New York

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

Authors

  • Chada Raji Reddy*

    a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad – 500 007, India
  • Enukonda Jithender

    a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad – 500 007, India
  • Ashita Singh

    b   Centre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad – 500 007, India   Fax: +91(40)27160512   Email: rajireddy@iict.res.in
  • Ramesh Ummanni*

    b   Centre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad – 500 007, India   Fax: +91(40)27160512   Email: rajireddy@iict.res.in
Further Information

Publication History

Received: 28 October 2013

Accepted after revision: 12 January 2014

Publication Date:
10 February 2014 (online)


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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.

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