Synfacts 2010(8): 0859-0859  
DOI: 10.1055/s-0030-1257747
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of RO5114436

Contributor(s): Philip Kocienski
X. Huang*, E. O’Brien, F. Thai, G. Cooper*
Roche Palo Alto, USA
Further Information

Publication History

Publication Date:
22 July 2010 (online)

Significance

RO5114436 is a chemokine receptor CCR5 antagonist that is a lead for the treatment of HIV and inflammatory disorders. The ­thirteen-step synthesis depicted features (1) a ­ruthenium-catalyzed asymmetric hydrogenation of an unprotected enamino ester using the (R)-MeOBIPHEP ligand and (2) a large-scale dipolar cycloaddition to generate the 3,7-diazabicyclo-[3.3.0]octane fragment H.