Enzymes and practical asymmetric synthesis

M. Bhupathy, D. L. Hughes, L. S. Amato, J. J. Bergan, J. L. Leazer, T. C. Lovelace, J. M. McNamara, R. A. Reamer, D. R. Sidler, E. J.J. Grabowski, P. J. Reider, I. Shinkai

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A practical, chemoenzymatic, four-step synthesis of the LTD4 antagonist MK-0679 is described. The key steps are enzymatic hydrolysis of the prochiral diester to the ester-acid in 99% enantiomeric excess followed by aluminum mediated amidation of the methyl ester to afford MK-0679 in high overall yield. This synthesis is superior to the synthesis of the racemate MK-0571.

Original languageEnglish (US)
Pages (from-to)1939-1944
Number of pages6
JournalPure and Applied Chemistry
Issue number12
StatePublished - Jan 1 1992
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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    Bhupathy, M., Hughes, D. L., Amato, L. S., Bergan, J. J., Leazer, J. L., Lovelace, T. C., McNamara, J. M., Reamer, R. A., Sidler, D. R., Grabowski, E. J. J., Reider, P. J., & Shinkai, I. (1992). Enzymes and practical asymmetric synthesis. Pure and Applied Chemistry, 64(12), 1939-1944. https://doi.org/10.1351/pac199264121939