Tetrahedron letters

Biomimetic cyclisation of prebrevetoxin polyepoxide models

DR Kelly, J Nally

Index: Kelly, David R.; Nally, James Tetrahedron Letters, 1999 , vol. 40, # 16 p. 3251 - 3254

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Citation Number: 9

Abstract

(E)-1, 3-Dihydroxyhex-4-ene and (E)-1, 3-dihydroxy-4-methylhex-4-ene undergo epoxidation with peracetic acid and in situ cyclisation to give a mixture of tetrahydro-furans and-pyrans, whereas comparable compounds lacking the allylic hydroxyl group give predominantly or exclusively tetrahydrofurans. These reactions model the first cyclisation of prebrevetoxin polyepoxides and demonstrate the regio-directing effect of the hydroxy ...