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Concise total syntheses of (–)-jorunnamycin A and (–)-jorumycin enabled by asymmetric catalysis
- Welin, Eric R;
- Ngamnithiporn, Aurapat;
- Klatte, Max;
- Lapointe, Guillaume;
- Pototschnig, Gerit M;
- McDermott, Martina SJ;
- Conklin, Dylan;
- Gilmore, Christopher D;
- Tadross, Pamela M;
- Haley, Christopher K;
- Negoro, Kenji;
- Glibstrup, Emil;
- Grünanger, Christian U;
- Allan, Kevin M;
- Virgil, Scott C;
- Slamon, Dennis J;
- Stoltz, Brian M
- et al.
Published Web Location
https://doi.org/10.1126/science.aav3421Abstract
The bis-tetrahydroisoquinoline (bis-THIQ) natural products have been studied intensively over the past four decades for their exceptionally potent anticancer activity, in addition to strong Gram-positive and Gram-negative antibiotic character. Synthetic strategies toward these complex polycyclic compounds have relied heavily on electrophilic aromatic chemistry, such as the Pictet-Spengler reaction, that mimics their biosynthetic pathways. Herein, we report an approach to two bis-THIQ natural products, jorunnamycin A and jorumycin, that instead harnesses the power of modern transition-metal catalysis for the three major bond-forming events and proceeds with high efficiency (15 and 16 steps, respectively). By breaking from biomimicry, this strategy allows for the preparation of a more diverse set of nonnatural analogs.
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