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

MA Brimble, YCW Liu, M Trzoss

Index: Brimble, Margaret A.; Liu, Yen-Cheng; Trzoss, Michael Synthesis, 2007 , # 9 p. 1392 - 1402

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Citation Number: 11

Abstract

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 ...