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Synfacts 2011(11): 1151-1151  
DOI: 10.1055/s-0031-1289255
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a γ-Secretase Modulator

Contributor(s): Philip Kocienski
C. E. Stivala, A. Zakarian*
University of California, Santa Barbara, USA
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

The synthesis of the γ-secretase modulator depicted illustrates an efficient enantio­selective alkylation of enediolates derived from arylacetic acids using the chiral lithium amide base H as a stereodirecting agent. The chiral base is required in stoichiometric amounts, but it is recoverable and easily prepared in two steps from styrene oxide (M. J. Frizzle et al. Org. Process Res. Dev. 2007, 11, 215).