Two lactone formation reactions from 1, 3-dioxin-4-ones having hydroxyalkyl group at the 6-position: Difference in ring opening and closure

…, J Sakaki, Y Sugita, S Yasuda, H Sakoda, C Kaneko

Index: Sato, Masayuki; Sakaki, Jun-ichi; Sugita, Yoshiaki; Yasuda, Sanae; Sakoda, Hiroko; Kaneko, Chikara Tetrahedron, 1991 , vol. 47, # 30 p. 5689 - 5708

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Citation Number: 35

Abstract

Two methods (A: ring opening to acylketenes followed by intramolecular ketene trapping and B: methoxide-mediated ring opening followed by cyclization of the hydroxy esters thus formed) have become available for the synthesis of lactones and/or cyclic ethers from 1, 3- dioxin-4-ones having 1-∼ 4-hydroxyalkyl group at the 6-position. Mechanism and scope of both methods have been clarified.