Journal
NATURE CHEMISTRY
Volume 7, Issue 3, Pages 234-240Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.2173
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Funding
- National Institutes of Health (NIH) [GM-099920, GM-067041]
- Vertex Pharmaceuticals, Inc.
- National Science Foundation [OCI-1053575]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1362519] Funding Source: National Science Foundation
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Chiral, dimeric natural products containing complex structures and interesting biological properties have inspired chemists and biologists for decades. A seven-step total synthesis of the axially chiral, dimeric tetrahydroxanthone natural product rugulotrosin A is described. The synthesis employs a one-pot Suzuki coupling/dimerization to generate the requisite 2,2'-biaryl linkage. Highly selective point-to-axial chirality transfer was achieved using palladium catalysis with achiral phosphine ligands. Single X-ray crystal diffraction data were obtained to confirm both the atropisomeric configuration and absolute stereochemistry of rugulotrosin A. Computational studies are described to rationalize the atropselectivity observed in the key dimerization step. Comparison of the crude fungal extract with synthetic rugulotrosin A and its atropisomer verified that nature generates a single atropisomer of the natural product.
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