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

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
› Author Affiliations
Further Information

Publication History

Received: 28 October 2013

Accepted after revision: 12 January 2014

Publication Date:
10 February 2014 (online)


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.

Supporting Information