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Hypervalent iodine oxidation: Synthesis of 5-substituted-2(5H)-furanones using iodosobenzene

✍ Scribed by Robert M. Moriarty; Radhe K. Vaid; Thomas E. Hopkins; Beena K. Vaid; Atilla Tuncay

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
254 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

Hypervalent iodine oxidation of Z-(trimethylsilyloxy)furan with iodosobenzeneboron bifluoride etherate in the presence of various nucleophiles yields 5-substituted-2(.5H)-furanones. 5Substituted-2(5H)-furanones are versatile intermediates for the synthesis of a number of important natural products and biologically active molecules. 23 Frequently, the presence of an unsaturated y-lactone is found to impart antibiotic properties.4p5 5-Substituted-2(5H)-furanones have also been used as dienophiles in asymmetric Diels-Alder reactions.6 The literature preparations of many useful 5-substituted-2(5H)-furanones are typically lengthy and do not always lend themselves to large scale reactions5 Recently we reported the use of hypervalent iodine for the synthesis of a-functionalized ketones and pdiketones.7*a In continuation of our efforts, we became interested in the functionalization of 2(5H)-furanones at the y-position starting with the precursor, 2-(trimethylsilyloxy)furan 1-9 We now report the use of icdosobenzene for the preparation of 5-substituted-2(5H)-furanones as exemplified in Scheme 1.

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