Abstract
Bisavenanthramide B-6 (2) is a highly substituted γ-lactam derived from oat leaves. Development of a new base-promoted anhydride Mannich reaction with N-sulfonylated imines that forms the core structure of 2 in a single step is presented. Further elaboration allows for a facile one-pot double Buchwald N-arylation to install the final rings onto the densely substituted γ-lactam core. This route provides the natural product in a longest linear sequence of nine steps.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1740-1743 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 18 |
| Issue number | 8 |
| DOIs | |
| State | Published - Apr 15 2016 |
ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
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Di Maso, M. J., Nepomuceno, G. M., St. Peter, M. A., Gitre, H. H., Martin, K. S., & Shaw, J. T. (2016). Synthesis of (±)-Bisavenanthramide B-6 by an Anionic Anhydride Mannich Reaction. Organic Letters, 18(8), 1740-1743. https://doi.org/10.1021/acs.orglett.6b00413