Download PDF
Synfacts 2006(12): 1195-1195  
DOI: 10.1055/s-2006-955594
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Hepatitis C Polymerase Inhibitor

Contributor(s): Philip Kocienski
D. Camp, C. F. Matthews, S. T. Neville, M. Rouns, R. W. Scott*, Y. Truong
Pfizer Global R&D, San Diego and Groton, USA
Further Information

Publication History

Publication Date:
22 November 2006 (online)

    Permissions and Reprints

Significance

The large-scale synthesis of the hepatitis C polymerase inhibitor shown features a Heck reaction [using 1.8 kg of Pd(OAc)2] to generate ketone D. Enantiopure intermediate F was generated by a very efficient classical resolution. Only 0.5 equivalent of (1R,2S)-1-amino-2-indanol was required to give F with an er > 99:1. The unwanted enantiomer could be recycled to give D by a retro-aldol reaction.