Total Synthesis of (-)-Maysine

A. I. Meyers, Kevin A. Babiak, Arthur L. Campbell, Daniel L. Comins, Michael P. Fleming, Rainer Henning, Manfred Heuschmann, James P. Hudspeth, John M. Kane, Paul J. Reider, Dennis M. Roland, Kimihiro Shimizu, Kyoshi Tomioka, Robert D. Walkup

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Abstract

A convergent synthesis of the natural macrocycle (-)-maysine (3) has been accomplished involving only a single separation of epimers at C-10. The scheme involved the preparation of three major fragments: (a) the western zone, 4; (b) the southern zone, 6; and (c) the northeastern zone in enantiomerically pure from (+)-37. Each of these components was coupled through the appropriate functionality leading to the target compound.

Original languageEnglish (US)
Pages (from-to)5015-5024
Number of pages10
JournalJournal of the American Chemical Society
Volume105
Issue number15
DOIs
StatePublished - Jul 1983
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Meyers, A. I., Babiak, K. A., Campbell, A. L., Comins, D. L., Fleming, M. P., Henning, R., Heuschmann, M., Hudspeth, J. P., Kane, J. M., Reider, P. J., Roland, D. M., Shimizu, K., Tomioka, K., & Walkup, R. D. (1983). Total Synthesis of (-)-Maysine. Journal of the American Chemical Society, 105(15), 5015-5024. https://doi.org/10.1021/ja00353a027