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Paper | Regular issue | Vol 53, No. 4, 2000, pp.777-784
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8744
Total Syntheses of Kurasoins A and B, Novel Protein Farnesyltransferase Inhibitors, and Absolute Structures of Kurasoins A and B

Tomoyasu Hirose, Toshiaki Sunazuka, Tian Zhi-Ming, Masaki Handa, Ryuji Uchida, Kazuro Shiomi, Yoshihiro Harigaya, and Satoshi Omura*

*Research Center for Biological Function, The Kitasato Institute and School of Pharmaceutical Sciences, Kitasato University, Shirokane, Tokyo 108-8642, Japan

Abstract

Asymmetric total syntheses of kurasoins A (1) and B (2), recently discovered protein farnesyltransferase (PFTase) inhibitors, have been achieved in seven steps from 2-(4-hydroxyphenyl)ethanol via the stereospecific alkylation of the chiral epoxide ((-)-7) and in four steps from phenylacetaldehyde via the coupling reaction of the chiral epoxide ((-)-13) with indole, respectively. The synthesis defined the (3S) absolute configuration of 1 and 2. The stereochemistry of the hydroxy group is important for eliciting PFTase inhibition.