Journal of Organic Chemistry 2005-01-07

Asymmetric synthesis of a prostaglandin D2 receptor antagonist.

Kevin R Campos, Michel Journet, Sandra Lee, Edward J J Grabowski, Richard D Tillyer

Index: J. Org. Chem. 70(1) , 268-74, (2005)

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Abstract

An asymmetric synthesis was developed for the production of a prostaglandin D(2) receptor antagonist for the treatment of allergic rhinitis. The stereogenic center was set using asymmetric allylic alkylation chemistry, and the core of the structure was constructed via Pd-catalyzed N-cyclization/Heck methodology. The synthesis relies on a late stage indoline oxidation which does not racemize the product.