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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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A multigram chemical synthesis of the gamma-secretase inhibitor LY411575 and its diastereoisomers.

An improved chemical synthesis of N-2((2S)-2-(3,5-difluorophenyl)-2-hydroxyethanoyl)-N1-((7S)-5-methyl-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-l-alaninamide (LY411,575, 9a), a known gamma-secretase inhibitor, is described. The key synthetic steps, which used no chiral chromatography in the entire sequence, involved (1) improved microwave-assisted synthesis of a seven-membered lactam (+/-)-(5,7-dihydro-6H-dibenz-[b,d]azepin-6-one 2, and (2) convenient isolation of pure LY411575 from a mixture of four diastereomers by simple flash silica gel chromatography. Starting from the resolved aminolactams 5a and 5b, all four diastereomers were produced in enantiomerically pure form.[1]

References

  1. A multigram chemical synthesis of the gamma-secretase inhibitor LY411575 and its diastereoisomers. Fauq, A.H., Simpson, K., Maharvi, G.M., Golde, T., Das, P. Bioorg. Med. Chem. Lett. (2007) [Pubmed]
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