Issue 11, 2009

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

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

Article information

Article type
Tutorial Review
Submitted
02 Mar 2009
First published
16 Sep 2009

Chem. Soc. Rev., 2009,38, 3160-3174

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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