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Mucochloric Acid: A Useful Synthon for the Selective Synthesis of 4-Aryl-3-chloro-2(5H)-furanones, (Z)-4-Aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones and 3,4-Diaryl-2(5H)-furanones

✍ Scribed by Fabio Bellina; Chiara Anselmi; Francesca Martina; Renzo Rossi

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
224 KB
Volume
2003
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

3,4‐Dichloro‐2(5__H__)‐furanone, which has been prepared efficiently from mucochloric acid, has been transformed selectively into 4‐aryl‐3‐chloro‐2(5__H__)‐furanones either by Suzuki‐ or Stille‐type reactions. These monochloro derivatives have been used as precursors either to (Z)‐4‐aryl‐5‐[1‐(aryl)methylidene]‐3‐chloro‐2(5__H__)‐furanones, including naturally occurring rubrolide M, or to unsymmetrical 3,4‐diaryl‐2(5__H__)‐furanones. Some 2(5__H__)‐furanone derivatives so prepared have been found to exhibit significant cytotoxic activity in vitro against the NCI three‐cell‐line panel, but limited cytotoxicity against the NCI human tumor 60 cell‐line panel. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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## Abstract Both symmetrical and unsymmetrical 3,4‐diaryl‐substituted 2(5__H__)‐furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)~2~/PCy~3~‐catalyzed Suzuki‐type arylation of readily available 3‐aryl‐4‐tosyloxy‐2(5__H__)‐furanones as the key step. The