Abstract
The structurally unique akuammiline alkaloid (+)-scholarisine A was synthesized in 14 steps from a known enone (15 steps from commercial materials) through a route empowered by a unique C-H arylation reaction to forge its polycyclic core. Additional key steps include a pyrone Diels-Alder reaction and a radical cyclization/Keck allylation to fashion the core cage polycycle and one of the molecule's quaternary centers, as well as the use of a carefully positioned pendant hydroxyl group to facilitate the chemoselective reduction of an extremely unreactive lactam in the presence of a readily reduced lactone.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 12964-12967 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 135 |
| Issue number | 35 |
| DOIs | |
| State | Published - Sep 4 2013 |
| Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
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Cite this
Smith, M. W., & Snyder, S. A. (2013). A concise total synthesis of (+)-scholarisine a empowered by a unique C-H arylation. Journal of the American Chemical Society, 135(35), 12964-12967. https://doi.org/10.1021/ja406546k