Synthetic Communications

Functicnalization of 4-Hydroxy-6-Methyl-2-Pyrone at C-5 Through [2, 3] Sigmatropic Rearrangements of Allylic Sulphonium Ylides

P March, M Moreno-Mañas, I Ripoll

Index: March, P. de; Moreno-Manas, M.; Ripoll, I. Synthetic Communications, 1984 , vol. 14, # 6 p. 521 - 532

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Citation Number: 9

Abstract

Functionalization at C-5 of the triacetic acid lactone methyl ether,J, has been achieved by a transfer from the C-6 position. Thus, treatment of sulfides 12 with an excess of ethyl diazoaceta- te provides the pyrones 5 through [2,3] sigmatropic rearrangements. ... 4-Hydroxy-6-methyl-2-pyrone (triacetic acid lactone) , l-, is a 1 simple polyketide which is easily prepared' from the industrially ... M 2. Therefore, the lactones ,l-andAshould be ideal precursors for