Synthesis of Methyl 7??Bromo??5??heptynoate??a building block for the carboxylic side chain of prostaglandins

…, M Henning, H Schick, S Schwarz

Index: Theil, Fritz; Henning, Mechthild; Schick, Hans; Schwarz, Sigfrid Journal fuer Praktische Chemie (Leipzig), 1985 , vol. 327, # 6 p. 917 - 922

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Abstract

Abstract Methyl 7-bromo-5-heptynoate (11) was synthesized in 8 steps using the alkylation of 1-(2H-tetrahydropyran-2-yloxy)-2-propyne with 1-bromo-4-chloro-butane as a key reaction step. Furthermore it was shown, that also the unprotected propargyl alcohol (12) can be C-alkylated with high chemoselectivity using 1-bromo-4-chloro-butane. In this way the number of necessary reaction steps could be reduced without decrease in the total ...