Seven-membered rings

Authors

Bill C. Hawkins, University of Otago
Alex C. Bissember, University of Tasmania
Steven M. Wales, University of the Sunshine Coast
Jack L.Y. Chen, Auckland University of Technology
Wade F. Petersen, University of Cape Town
Andrew J. Tague, University of Wollongong
Cassandra L. Fleming, Auckland University of Technology
Nicholas J. Green, University of Otago
James P. Shephard, Monash University
Mark D. Johnstone, Auckland University of Technology
Samuel D.L. Harrison, University of Otago
Andrew P. Cording, University of Otago

Publication Name

Progress in Heterocyclic Chemistry

Abstract

Progress in the synthesis of seven-membered heterocycles bearing up to and including three N, O, or S heteroatoms continues unabated. The application of classical ring expansion strategies continues to be investigated. However, many original ring expansion approaches were also developed to synthesize these frameworks. Cyclization methodology remains a cornerstone in the construction of seven-membered heterocycles, with Dieckmann cyclizations, Friedel–Crafts alkylations and acylations, Pictet–Spengler-type and Bischler–Napieralski-type reactions, and ring-closing metatheses successfully deployed. Enabling cascade reactions and powerful catalytic processes continue to enhance access to seven-membered heterocycles. Total syntheses of natural products containing oxepane, azepane, and 1,3,6-oxadiazepane cores were completed. There was only one report of the preparation of a seven-membered ring containing four N, O, or S heteroatoms–a tricyclic tetrazepine.

Open Access Status

This publication is not available as open access

Volume

35

First Page

569

Last Page

628