JP2 - Enatioselective Organo-SOMO Catalysis: A Proposed...

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Enatioselective Organo-SOMO Catalysis: A Proposed Synthesis Route for Zoloft® David Grauer dgrauer@princeton.edu With the FDA taking more serious interest in enantiomerically pure and consistent substances, an efficient method for producing these stereocenters is needed. Until now, syntheses have relied on resolution of racemic material rather than enantioselective reaction methods for the creation of most stereocenters. The synthesis of the anti- depressant Zoloft® is no exception. The current synthesis for the production of this multi-million dollar drug uses enantioselective reduction of rac- tetralone during the last two synthetic steps. Until recently, the synthesis relied on post-reduction enantiomeric purification, an inherently inefficient and wasteful process (Quallich, 2005). Zoloft® is a SSRI (selective serotonin reuptake inhibitor) type anti-depressant that functions much as its type name implies. Zoloft® has a degree of structural homology with serotonin and works by blocking the synaptic serotonin uptake receptors in the brain. By blocking uptake, Zoloft® triggers an increase in synaptic serotonin levels. This paper will discuss a proposed synthetic pathway utilizing enantioselective organo-SOMO catalysis to selectively create the two stereocenters on Zoloft®. Figure 1: SOMO activation and catalyst orientation (Beeson, et. al., 2007; Mangion, et al., 2004). QuickTime and a TIFF (Uncompressed) decompressor are needed to see this picture. QuickTime and a TIFF (Uncompressed) decompressor are needed to see this picture. As indicated in Figure 1, SOMO catalysis relies on the activation of aldehydes with activated secondary amine catalysts. These catalysts force the reactants to adopt a specific orientation as they react, thus producing a specific and consistent stereochemistry in the products. Design Plan
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This essay was uploaded on 12/19/2007 for the course CHM 371 taught by Professor Andrewb.bocarsly,istvanpelczer,prasads.lakkaraju during the Fall '07 term at Princeton.

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JP2 - Enatioselective Organo-SOMO Catalysis: A Proposed...

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