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Tutorial Review
Chem. Soc. Rev., 2009, 38, 3160 - 3174, DOI: 10.1039/b816705m
Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids
Kenneth A. Miller and Robert M. Williams
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.
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