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
. 2003:(1):127-137.
doi: 10.1055/s-2003-36234.

Strategies for the Preparation of Differentially Protected ortho-Prenylated Phenols

Christophe Hoarau  1 , Thomas R R Pettus
Affiliations

Strategies for the Preparation of Differentially Protected ortho-Prenylated Phenols

Christophe Hoarau et al. Synlett. 2003.

Abstract

A new process for ortho-prenylation of phenols is presented within the context of known methods. All of the processes are briefly assessed with regards to the substitution patterns and accompanying functional groups tolerated by each strategy. The conclusion reached is that a new procedure using ortho-quinone methides, for which an experimental protocol is provided, offers the greatest generality and flexibility in the preparation of ortho-prenylated phenol derivatives.

PubMed Disclaimer

Figures

Figure 1
Figure 1
All of the analogs of differentially protected ortho-prenylated dihydroxyphenol nuclei (PH).
Figure 2
Figure 2
Differentially protected dihydroxyphenols that are commercially available.
Scheme 1
Scheme 1
The general DoM strategy
Scheme 1a
Scheme 1a
Scheme 1b
Scheme 1b
Scheme 1c
Scheme 1c
Scheme 1d
Scheme 1d
Scheme 2
Scheme 2
General metal exchange strategies for prenylation
Scheme 2a
Scheme 2a
Scheme 2b
Scheme 2b
Scheme 2c
Scheme 2c
Scheme 2d
Scheme 2d
Scheme 2e
Scheme 2e
Scheme 3
Scheme 3
General phenoxide C-prenylation strategy
Scheme 3a
Scheme 3a
Scheme 3b
Scheme 3b
Scheme 4
Scheme 4
The general Claisen rearrangement strategy
Scheme 4a
Scheme 4a
Scheme 4b
Scheme 4b
Scheme 5
Scheme 5
General Friedel–Crafts prenylation strategy
Scheme 5a
Scheme 5a
Scheme 5b
Scheme 5b
Scheme 5c
Scheme 5c
Scheme 5d
Scheme 5d
Scheme 5e
Scheme 5e
Scheme 6
Scheme 6
General Birch reductions strategy
Scheme 6a
Scheme 6a
Scheme 7
Scheme 7
1,4-Conjugate addition strategy
Scheme 7a
Scheme 7a
Scheme 8
Scheme 8
General benzylic coupling strategy
Scheme 8a
Scheme 8a
Scheme 8b
Scheme 8b
See this image and copyright information in PMC

References

    1. Brandt U. Biofactors. 1999;9:95. - PubMed
    1. Fukui H, Feroj Hassan AFM, Ueoka T, Kyo M. Phytochemistry. 1998;47:1037.
    1. Mori K, Waku M, Sakakibara M. Tetrahedron. 1985;41:2825.
    1. Basset C, Sherwood RT, Kepler JA, Hamilton PB. Phytopathology. 1967;57:1046.
    2. Wächter GA, Hoffmann JJ, Furbacher T, Blake ME, Timmermann BN. Phytochemistry. 1999;52:1469. - PubMed
    1. Ghirtis K, Pouli N, Marakos P, Skaltsounis A-L, Leonce S, Caignard DH, Atassi G. Heterocycles. 2000;53:93. - PubMed

LinkOut - more resources