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. 2009;48(38):7025-9.
doi: 10.1002/anie.200902761.

Direct, chemoselective N-tert-prenylation of indoles by C-H functionalization

Michael R Luzung  1 , Chad A Lewis, Phil S Baran
Affiliations

Direct, chemoselective N-tert-prenylation of indoles by C-H functionalization

Michael R Luzung et al. Angew Chem Int Ed Engl. 2009.
No abstract available

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Figures

Figure 1
Figure 1
Inspiration from a failed campaign in the stephacidin total synthesis (A), currently known direct prenylation modalities (B), and the known route to N-tert-prenyl indoles compared to the C–H functionalization alternative (C). Boc = tert-butoxycarbonyl, DDQ = 2,3-dichloro-5,6-dicyano-p-benzoquinone.
Figure 2
Figure 2
Scalable, one-step routes to previously employed N-tert-prenyl indole intermediates.
Figure 3
Figure 3
Mechanistic probe experiments (A), and postulated mechanism (B).
Figure 4
Figure 4
Informative products using prenyl acetate or cis-2-butene as olefin source.
See this image and copyright information in PMC

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