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Synthesis 2021; 53(01): 65-78
DOI: 10.1055/s-0040-1707385
DOI: 10.1055/s-0040-1707385
short review
Synthetic Approaches to Non-Tropane, Bridged, Azapolycyclic Ring Systems Containing Seven-Membered Carbocycles
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
Key words
alkaloids - heterocycles - rearrangements - natural products - cycloheptane - bridged bicyclicPublication History
Received: 01 July 2020
Accepted after revision: 14 August 2020
Article published online:
11 September 2020
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