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Synthesis 2010(1): 115-119  
DOI: 10.1055/s-0029-1217096
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© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis and Biological Studies of the C2 and C3 Epimer and the Enantiomer of Pachastrissamine (Jaspine B)

G. Jayachitraa, N. Sudhakara, Ravi Kumar Anchooria, B. Venkateswara Rao*a, Sayantani Royb, Rajkumar Banerjeeb
a Organic Division III, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27193003; e-Mail: venky@iict.res.in;
b Lipid Science and Technology, Indian Institute of Chemical Technology, Hyderabad 500007, India
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Publication History

Received 11 August 2009
Publication Date:
03 November 2009 (online)

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Abstract

The synthesis of the C2 and C3 epimer and also the enantiomer of jaspine B from d-glucose is reported. The cytotoxicity of these isomers along with jaspine B and its C2 epimer on MCF7 cells has been correlated with commercially available anticancer drug Epirubicin.

Key words

cytotoxicity - d-glucose - pachastrissamine - jaspine B - Mitsunobu inversion - Wittig olefination

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