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. 2011 Mar 23;133(11):3832-5.
doi: 10.1021/ja200437g. Epub 2011 Feb 25.

Overturning indolyne regioselectivities and synthesis of indolactam V

Sarah M Bronner  1 , Adam E Goetz, Neil K Garg
Affiliations

Overturning indolyne regioselectivities and synthesis of indolactam V

Sarah M Bronner et al. J Am Chem Soc. .

Abstract

We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4,5-indolynes. Our approach utilizes simple computations to predict regioselectivity in reactions of unsymmetrical arynes. With this methodology, novel benzenoid-substituted indoles can be accessed with significant regiocontrol. Furthermore, the technology provides an unconventional tactic for the synthesis of C4-substituted indole alkaloids, as demonstrated by a synthesis of indolactam V.

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Figures

Figure 1
Figure 1
C4-substituted alkaloids 1–4 and indolynes 5 and 6.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
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References

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