Tetrahedron

Synthesis of precursors of phomactins using [2, 3]-Wittig rearrangements

PDP Shapland, EJ Thomas

Index: Shapland, Peter D.P.; Thomas, Eric J. Tetrahedron, 2009 , vol. 65, # 21 p. 4201 - 4211

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Citation Number: 17

Abstract

o-Toluic acid has been converted into methyl (8RS, 9SR)-7-(bromomethyl)-8, 9-dimethyl-1, 4- dioxaspiro [4.5] dec-6-ene-8-carboxylate, the stereochemical defining step being a conjugate addition of lithium dimethylcuprate to a cyclohexadienone prepared using a Birch reduction followed by an allylic oxidation. Displacement of the bromide with various propargylic alcohols followed by reduction of the ester and protection of the primary ...

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