Adaptation of a Small-Molecule Hydrogen-Bond Donor Catalyst to an Enantioselective Hetero-Diels–Alder Reaction Hypothesized for Brevianamide Biosynthesis

نویسندگان

  • Daniel J. Sprague
  • Benjamin M. Nugent
  • Ryan A. Yoder
  • Brandon A. Vara
  • Jeffrey N. Johnston
چکیده

Chiral diamine-derived hydrogen-bond donors were evaluated for their ability to effect stereocontrol in an intramolecular hetero-Diels-Alder (HDA) reaction hypothesized in the biosynthesis of brevianamides A and B. Collectively, these results provide proof of principle that small-molecule hydrogen-bond catalysis, if even based on a hypothetical biosynthesis construct, holds significant potential within enantioselective natural product synthesis.

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عنوان ژورنال:

دوره 17  شماره 

صفحات  -

تاریخ انتشار 2015