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. 2010 Jun 16;132(23):7870-1.
doi: 10.1021/ja103472a.

Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction

Tejas P Pathak  1 , Keith M Gligorich, Bryan E Welm, Matthew S Sigman
Affiliations

Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction

Tejas P Pathak et al. J Am Chem Soc. .

Abstract

A unique alkene difunctionalization reaction that allows rapid construction of molecular complexity around the biologically relevant indole framework has been developed. The reaction proceeds with up to 87% yield, 99:1 er, and >20:1 dr. Evaluation of several of the compounds revealed promising anticancer activity against MCF-7 cells.

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Figures

Figure 1
Figure 1
(a) Relative activity of new compounds in MCF-7 cells. (b) Cell cycle analysis of 2c and 2f at 48h.
Scheme 1
Scheme 1
Proposed mechanism for tandem oxypalladation/electrophilic aromatic substitution process.
Scheme 2
Scheme 2
Accessing interesting indole core structures.
See this image and copyright information in PMC

References

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    1. Jensen KH, Pathak TP, Zhang Y, Sigman MS. J. Am. Chem. Soc. 2009;131:17074. - PMC - PubMed

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    1. a) See the supporting information for more detail. b) See footnote of Table 1 for detailed optimized conditions.

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