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Synfacts 2010(10): 1095-1095
DOI: 10.1055/s-0030-1258073
DOI: 10.1055/s-0030-1258073
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Prostaglandin D2 Receptor Antagonist
M. Tudge*, C. G. Savarin, K. DiFelice, P. Maligres, G. Humphrey, B. Reamer, D. M. Tellers, D. Hughes
Merck & Co., Rahway, USA
Further Information
Publication History
Publication Date:
22 September 2010 (online)
Significance
An efficient kilogram-scale synthesis of the target prostaglandin D2 receptor antagonist features a Friedel-Crafts cyclization of an iminopyrrole to generate the azaindole core in D. Key steps are (1) a very efficient asymmetric hydrogenation to install the single stereogenic center (G → H) and (2) a mild sulfenylation using the shelf-stable N-arylthiophthalimide I.