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Synfacts 2009(8): 0831-0831  
DOI: 10.1055/s-0029-1217574
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of IBR2 Analogues

Contributor(s): Philip Kocienski
X.-L. Qiu*, J. Zhu, G. Wu, W.-H. Lee*, A. R. Chamberlain
University of California, Irvine, USA
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

IBR2 (3,4-dehydro-D) is a lead inhibitor of Rad51, an enzyme overexpressed in rapidly proliferating cancer cells, that plays an essential role in DNA damage repair and cell proliferation. IBR2 is unstable and 16 analogues were prepared in the search for greater stability and activity. The noteworthy step in the synthesis depicted is the asymmetric Friedel-Crafts reaction of the sulfinimine F with indole mediated by the thiourea G to give H in 55% yield and er > 99:1.