Tetrahedron Letters

Synthesis of exo enol ether-cyclic ketal isomers of substituted furanmethanol structures related to marine furanocembranoids

Y Li, G Pattenden, J Rogers

Index: Li, Yi; Pattenden, Gerald; Rogers, Joseph Tetrahedron Letters, 2010 , vol. 51, # 9 p. 1280 - 1283

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Citation Number: 18

Abstract

Oxidations of the 2-alkenylfurans 8a and 8b, using peroxy reagents, lead to the dienedione 9 and the furan epoxide 10, respectively. Treatment of the epoxide 10 with p-TSA in MeOH produces the enol ether cyclic ketal 12, which is rapidly isomerised to the furanmethanol ...