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Issue 11, 2009
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Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids

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Abstract

The bicyclo[2.2.2]diazaoctane ring system is common to a number of highly biologically active secondary metabolites isolated from numerous species of fungi. In this tutorial review, we describe the varied synthetic approaches that have been employed to construct this ring system in the course of recent total synthesis endeavors, and this review should be of interest to synthetic organic chemists and natural product chemists. Detailed herein are a number of synthetic disconnections including intramolecular SN2′ cyclizations, biomimetic Diels–Alder reactions, radical cyclizations, and cationic cascade reactions.

Graphical abstract: Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids

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Publication details

The article was received on 02 Mar 2009 and first published on 16 Sep 2009


Article type: Tutorial Review
DOI: 10.1039/B816705M
Citation: Chem. Soc. Rev., 2009,38, 3160-3174
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    Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids

    K. A. Miller and R. M. Williams, Chem. Soc. Rev., 2009, 38, 3160
    DOI: 10.1039/B816705M

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