An efficient Synthesis of Acetylenic γ??and δ??Hydroxy Ketones, γ??and δ??keto acids, and γ??diketones via addition of 1??alkinyllithium compounds to γ??and δ??lactones

C Wedler, H Schick

Index: Wedler, Christine; Schick, Hans Journal fuer Praktische Chemie/Chemiker-Zeitung, 1993 , vol. 335, # 5 p. 410 - 414

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Citation Number: 4

Abstract

Abstract 2-Hydroxy-6-alkyn-5-ones 3, 1-hydroxy-5-alkyn-4-ones 4, and 1-hydroxy-6-alkyn-5- ones 5 are conveniently obtained in excellent yields through a highly selective monoaddition of an 1-alkynyllithium compound 2 to γ-valerolactone (1a), γ-butyrolactone (1b) or δ-valerolactone (1c). They are oxidized by pyridinium dichromate or Jones reagent to the corresponding acetylenic 1, 4-diketones 6, 4-oxo carboxylic acids 7, and 5-oxo ...