Issue 1, 1996

A cascade radical macrocyclisation–transannulation approach towards the construction of ring-fused tricycles and polycycles

Abstract

Treatment of the iodo trienone 6 with Bu3SnH–AIBN results in the formation of the angular 5,7,5-ring-fused tricyclic ketone 20 by way of a novel sequential 13-endo-trig macrocyclisation followed by two successive 5-exo-trig transannulation processes, viz 7→8→/18/19→20. The cis-anti-trans stereochemistry of 20 was established from an X-ray crystal structure determination of the corresponding 2,4-dinitrophenylhydrazone. By contrast, treatment of the iodo trienone 21 with Bu3SnH–AIBN, under the same conditions, led to the substituted cyclopropane 33 (instead of the hoped-for tricyclic ketone 22), and only the product 38 of macrocyclisation (without further transannulation to the triquinane 24) was produced when the iodo trienone 23 was treated similarly.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1996, 21-29

A cascade radical macrocyclisation–transannulation approach towards the construction of ring-fused tricycles and polycycles

M. J. Begley, G. Pattenden, A. Smithies, D. Tapolczay and D. S. Walter, J. Chem. Soc., Perkin Trans. 1, 1996, 21 DOI: 10.1039/P19960000021

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