Synthesis 2021; 53(01): 65-78
DOI: 10.1055/s-0040-1707385
short review

Synthetic Approaches to Non-Tropane, Bridged, Azapolycyclic Ring Systems Containing Seven-Membered Carbocycles

Aaron H. Shoemaker
,
Lafayette College, Department of Chemistry, 701 Sullivan Road, Easton, PA 18042, USA   Email: griffitd@lafayette.edu
› Author Affiliations
We thank the donors of the American Chemical Society Petroleum Research Fund (Grant No. 59202-UNI1) for financial support of our research program.


Dedicated in memory of Prof. Gilbert Stork

Abstract

This Short Review highlights various synthetic approaches to bridged azabicyclic ring systems containing seven-membered carbocyclic rings. Such ring systems are common to a number of biologically active natural products. The seven-membered ring in such systems is generally formed in one of four ways: 1) cyclization of an acyclic precursor; 2) ring expansion or rearrangement of a different ring size; 3) cycloaddition; and 4) use of a synthetic building block with the seven-membered ring already present. Representative examples of each approach from both total synthesis and methodological studies are discussed, with an emphasis on work published

in the last twenty years.

1 Introduction

2 Cyclization Reactions

3 Ring Expansions and Rearrangements

4 Cycloadditions

5 Strategies Involving Seven-Membered Ring Building Blocks

6 Conclusion



Publication History

Received: 01 July 2020

Accepted after revision: 14 August 2020

Publication Date:
11 September 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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