A Facile Synthesis of Aryl Spirodioxines Based on a 3H,3′H-2,2′-Spiro­bi(benzo[b][1,4]dioxine) Skeleton

Margaret A. Brimble; Yen-Cheng (William) Liu; Michael Trzoss

doi:10.1055/s-2007-966016

PAPER

A Facile Synthesis of Aryl Spirodioxines Based on a 3H,3′H-2,2′-Spirobi(benzo[b][1,4]dioxine) Skeleton

Margaret A. Brimble*, Yen-Cheng (William) Liu, Michael Trzoss
Department of Chemistry, University of Auckland, 23 Symonds St., 1142 Auckland, New Zealand
Fax: +64(9)3737422; e-Mail: m.brimble@auckland.ac.nz;

Abstract

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Abstract

The synthesis of a series of 6,6-bisbenzannulated spiroketals containing a 3H,3′Η-2,2′-spirobi(benzo[b][1,4]dioxine) ring system is reported. The key step involves addition of a monobenzyl-protected catechol to the epoxide unit of a glycidol bearing a benzyl-protected catechol. The resultant alcohol adduct is oxidized to a ketone that then undergoes hydrogenation and acid-catalyzed cyclization to produce the desired spirodioxines.

Key words

bisbenzannulated spiroketals - benzyl ether - catechol - epoxide - spirodioxines

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References

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A Facile Synthesis of Aryl Spirodioxines Based on a 3H,3′H-2,2′-Spiro­bi(benzo[b][1,4]dioxine) Skeleton

A Facile Synthesis of Aryl Spirodioxines Based on a 3H,3′H-2,2′-Spirobi(benzo[b][1,4]dioxine) Skeleton