Journal
SCIENCE
Volume 363, Issue 6424, Pages 270-+Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.aav3421
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Funding
- NIH National Institute of General Medical Sciences [R01 127972]
- Margaret E. Early Medical Research Trust
- NSF under the CCI Center for Selective C-H Functionalization [CHE-1700982]
- Teva Pharmaceuticals Marc A. Goshko Memorial Grant Program
- California Institute of Technology RI2 Program
- American Cancer Society [PF-16-011-01-CDD]
- Royal Thai Government Scholarship program
- German Academic Exchange Service
- Swiss National Science Foundation
- Erwin Schroedinger Fellowship from the Austrian Science Fund (FWF) [J 3893-N34]
- California HIV/AIDS Research Program
- Knud Hojgaards Fond
- Oticon Fonden
- Feodor Lynen Research Fellowship from the Alexander von Humboldt Foundation
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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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