Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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

PubMed Disclaimer

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

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. For prenylated indole alkaloid reviews: Williams RM, Stocking EM, Sanz-Cervera JF. Top Curr Chem. 2000;209:97–173.Scholz U, Winterfeldt E. Nat Prod Rep. 2000;17:349–366.

    1. Baran PS, Guerrero CA, Ambhaikar NB, Hafensteiner BD. Angew Chem Int Ed. 2005;44:606–609. - PubMed
    2. Baran PS, Guerrero CA, Ambhaikar NB, Hafensteiner BD. Angew Chem. 2005;117:612–615. - PubMed
    3. Baran PS, Guerrero CA, Hafensteiner BD, Ambhaikar NB. Angew Chem Int Ed. 2005;44:3892–3895. - PubMed
    4. Angew Chem. 2005;117:3960–3963.
    5. Baran PS, Hafensteiner BD, Ambhaikar NB, Guerrero CA, Gallagher JD. J Am Chem Soc. 2006;128:8678–8693. - PubMed
    1. Baran PS, Corey EJ. J Am Chem Soc. 2002;124:7904–7905. - PubMed
    1. Takase S, Kawai Y, Uchida I, Tanaka H, Aoki H. Tetrahedron. 1985;41:3037–3048.
    2. Tan GH, Zhu X, Ganesan A. Org Lett. 2003;5:1801–1803. - PubMed
    3. López-Alvarado P, Caballero E, Avendaño C, Menéndez JC. Org Lett. 2006;8:4303–4306. - PubMed
    1. Marsden SP, Depew KM, Danishefsky SJ. J Am Chem Soc. 1994;116:11143–11144.
    2. Kimura M, Futamata M, Mukai R, Tamaru Y. J Am Chem Soc. 2005;12:4592–4593. - PubMed

Publication types

Substances

LinkOut - more resources