Synthetic approaches to the bicyclo[2.2.2]diazaoctane ring system common to the paraherquamides, stephacidins and related prenylated indole alkaloids.
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 S(N)2' cyclizations, biomimetic Diels-Alder reactions, radical cyclizations, and cationic cascade reactions.
Department of Chemistry, Colorado State University, Fort Collins, CO 80523-1872, USA.
Kenneth A
KA
Miller
Robert M
RM
Williams
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D003979:Diazonium Compounds / Q000138:chemical synthesis*; D026121:Indole Alkaloids; D007212:Indolizines; D009795:Octanes / Q000138:chemical synthesis*; D054876:Prenylation; D013141:Spiro Compounds
D001643:Bridged Bicyclo Compounds; D003979:Diazonium Compounds; D026121:Indole Alkaloids; D007212:Indolizines; D009795:Octanes; D013141:Spiro Compounds; C470895:stephacidin A; C063985:paraherquamide; C026728:octane