A stereoselective palladium/copper-catalyzed route to isoprenoids: synthesis and biological evaluation of 13-methylidenefarnesyl diphosphate

…, U Krishnan, JM Dolence, CD Poulter

Index: Gibbs, Richard A.; Krishnan, Usha; Dolence, Julia M.; Poulter, C. Dale Journal of Organic Chemistry, 1995 , vol. 60, # 24 p. 7821 - 7829

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Citation Number: 76

Abstract

The novel farnesyl diphosphate (FPP) analog 13-methylidenefarnesyl diphosphate (3-VFPP, 4) was designed as a potential mechanism-based inhibitor of the FPP-utilizing enzyme protein-farnesyl transferase (PFTase). A six-step stereoselective route to 3-VFPP is described. The key step in the synthetic sequence involved the stereoselective coupling of vinyl triflate 16 with vinyltributyltin using Pd (AsPh3) 2 and CUI as catalysts to afford ...