Squalene synthetase inhibitors: synthesis of sulfonium ion mimics of the carbocationic intermediates

AC Oehlschlager, SM Singh…

Index: Oehlschlager, Allan C.; Singh, Shankar M.; Sharma, Sunaina Journal of Organic Chemistry, 1991 , vol. 56, # 12 p. 3856 - 3861

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Citation Number: 39

Abstract

Synthesis of sulfonium ion mimics 16 and 16 of the carbocationic intermediates 3 and 7, respectively, presumed to be involved in the squalene synthetase catalyzed rearrangement of farnesyl pyrophosphate (l), is reported. Synthesis of 15 involved combination of homogeranyl sulfide with ethyl a-bromoacetate through use of the thallium salt or via the combination of the copper enolate of ethyl acetate and homogeranyl thiosulfonate. ...