Tetrahedron

Alkylation reactions of propargyl alcohol; improved routes to prostaglandin α-side chain precursors

G Casy, M Furber, KA Richardson, GR Stephenson…

Index: Casy, Guy; Furber, Mark; Richardson, Kevan A.; Stephenson, Richard G.; Taylor, Richard J.K. Tetrahedron, 1986 , vol. 42, # 21 p. 5849 - 5856

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Citation Number: 12

Abstract

Alkylation reactions of the dilithio derivative of propargyl alcohol and the lithio derivative of tetrahydropyranyl protected propargyl alcohol have been explored in order to develop improved synthetic routes to the key prostaglandin α-side chain precursor methyl 7- hydroxyhept-5-ynoate (5). The use of methyl 4-bromobutanoate or the lithium salt of 4- bromobutanoic acid in these reactions did not produce the required products whereas ...