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Synfacts 2011(9): 0927-0927
DOI: 10.1055/s-0030-1260913
DOI: 10.1055/s-0030-1260913
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of a γ-Secretase Inhibitor
Contributor(s):Philip KocienskiJ. Su*, H. Tang, B. A. McKittrick
Merck Research Laboratory, Kenilworth, USA
Stereoselective Synthesis of C-6 Hydroxy Tricyclic Sulfone as a γ-Secretase Inhibitor
Tetrahedron Lett. 2011, 52: 3382-3385
Merck Research Laboratory, Kenilworth, USA
Stereoselective Synthesis of C-6 Hydroxy Tricyclic Sulfone as a γ-Secretase Inhibitor
Tetrahedron Lett. 2011, 52: 3382-3385
Further Information
Publication History
Publication Date:
19 August 2011 (online)
Key words
γ-secretase inhibitors - Suzuki-Miyaura coupling - SNAr reaction - epoxide opening
Significance
γ-Secretase inhibitors are of interest for the treatment of Alzheimer’s disease. The key step in the synthesis of the target γ-secretase inhibitor is the stereoselective opening of the epoxide E using a (triarylthio)boron reagent F derived from reaction of BH3 with p-chlorobenzenethiol.
Comment
The cis stereochemistry in H derives from prior coordination of the (triarylthio)boron reagent to the epoxide oxygen in E followed by epoxide ring opening and intramolecular transfer of an arylthio group to the resultant carbocation G.