Total synthesis of tetracyclines. 1 III. 2 synthesis of a tricyclic model system

RG WILKINSON, TL FIELDS…

Index: Wilkinson,R.G. et al. Journal of Organic Chemistry, 1961 , vol. 26, p. 637 - 643

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Citation Number: 8

Abstract

The starting material for this total synthesis, 4-chloro-3-methylaniole (VIII) O was converted to Zchloro-5methoxybenzyl bromide (IX) in good yield by two methods. The longer route involved permanganate oxidation to 2-chloro-5-methoxybenzoic acidlQ conversion to its methyl ester, lithium aluminum hydride reduction to the benzyl alcohol, and replacement of the hydroxyl group using phosphorus tribromide to give the benzyl bromide (IX), l0 a low ...