Volume 20, Issue 2
Heterocyclic Compounds
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ChemInform Abstract: Radical Cyclizations onto 2(5H)-Furanone and Maleate Electrophores Leading to Spiro- and Linear-Fused γ-Lactone Ring Systems.

T. HARRISON

T. HARRISON

Dep. Chem., Univ. Nottingham, Nottingham NG7 2RD, UK

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G. PATTENDEN

G. PATTENDEN

Dep. Chem., Univ. Nottingham, Nottingham NG7 2RD, UK

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P. L. MYERS

P. L. MYERS

Dep. Chem., Univ. Nottingham, Nottingham NG7 2RD, UK

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First published: January 10, 1989

Abstract

Dimethylmaleic anhydride (I) is reduced to give the 4-hydroxy-2-butenolide (II) and then converted to the ether (IV) which undergoes radical-induced cyclization, forming the bicyclic acetal (V).

ChemInform Abstract

Dimethylmaleic anhydride (I) is reduced to give the 4-hydroxy-2-butenolide (II) and then converted to the ether (IV) which undergoes radical-induced cyclization, forming the bicyclic acetal (V). This is oxidized with MCPBA to yield the fused bislactone (VI). Similar lactones such as (VIII) or (X) are prepared in an analogous manner.

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