Preparation and reactions of 2-(alkoxy)-1-(alkyl or arylthio) vinyllithium. Application in the synthesis of 9-desoxo-9-thiaprostaglandins

I Vlattas, L Della Vecchia, AO Lee

Index: Vlattas,I. et al. Journal of the American Chemical Society, 1976 , vol. 98, p. 2008 - 2010

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Citation Number: 44

Abstract

R=-(CH2) 5CN a, X= H, Y= OH b, X= OH; Y= H CHO). The corresponding acetals 8 (Y= CH (OEt) 2) are analogously prepared (p-TsOH, EtOH, 5 min, 0'). We have examined the reaction of 2 with epoxides. In THF at-70, the anion 2a reacts smoothly with ethylene oxide to yield 6 (R= Ph R'= H) in good yield. Under similar conditions, the alkylation of 2a with propylene oxide is sluggish. The alkylation, however, proceeds well in the presence of ...