Tetrahedron letters

Substituted 1, 7-dioxabicyclo [3.3. 0] octanes: New easy access to the perhydrofurofuran core of aflatoxins and analogues

F Alonso, E Lorenzo, M Yus

Index: Alonso, Francisco; Lorenzo, Emilio; Yus, Miguel Tetrahedron Letters, 1997 , vol. 38, # 12 p. 2187 - 2190

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Citation Number: 43

Abstract

The reaction of 3-chloro-2-(chloromethyl)-1-propene (1) with lithium and a catalytic amount of naphthalene in the presence of different carbonyl compounds in THF a− 78dgC affords, after hydrolysis, the corresponding methylenic diols 2, which by a tandem hydroboration- oxidation with hydrogen peroxide followed by treatment with PCC (for ketone derivatives) or RuCl2 (PPh3) 3 (for aldehyde derivatives) yields the expected perhydrofurofurans 3.