Stereospecific synthesis and biological evaluation of farnesyl diphosphate isomers

Y Shao, JT Eummer, RA Gibbs

Index: Shao, Ying; Eummer, Jeffrey T.; Gibbs, Richard A. Organic Letters, 1999 , vol. 1, # 4 p. 627 - 630

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Citation Number: 35

Abstract

A unified, stereospecific synthetic route to the three geometric isomers of (E, E)-farnesyl diphosphate (E, E-FPP)(1, 2, and 3) has been developed. The key feature of this synthesis is the ability to control the stereochemistry of triflation of the β-ketoester 10 to give either 11 or 14. Preliminary evaluation of these compounds with protein-farnesyl transferase indicates that 1 and 2 are surprisingly effective substrates; however, Z, Z-FPP (3) is a poor substrate ...