A New Class of Tröger’s
Base Analogues Bearing Spiro[4.5] Lactone Straps

Andrew B. Mahon; Donald C. Craig; Andrew C. Try

doi:10.1055/s-0028-1083341

PAPER

A New Class of Tröger’s Base Analogues Bearing Spiro[4.5] Lactone Straps

Andrew B. Mahon^a, Donald C. Craig^b, Andrew C. Try*^a
^a Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, NSW 2109, Australia
Fax: +61(2)98508313; e-Mail: andrew.try@mq.edu.au;
^b School of Chemistry, University of New South Wales, NSW 2052, Australia

Abstract

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Abstract

A protocol for the introduction of spiro[4.5] lactone straps onto the Tröger’s base scaffold has been developed. The conversion was found to be most efficient when an appropriate carboxylic acid derivative reacted with 5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocines. Whilst phthaloyl dichloride was the main strap-forming precursor used, other 1,2-unsaturated dicarboxylic acids could be used in the presence of N,N′-dicyclohexylcarbodiimide.

Key words

Tröger’s base - lactones - amines - cyclization - spiro compounds

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References

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