Abstract
Total syntheses of the dimeric tetrahydroxanthone natural products secalonic acids A and D are described. Key steps involve kinetic resolution of the tetrahydroxanthone core structure using homobenzotetramisole catalysis and late-stage copper(I)-mediated homodimerization of complex aryl stannane monomers. It takes two: Concise syntheses of the natural products secalonic acids A and D using copper(I)-mediated dimerization of complex aryl stannane monomers to construct the requisite 2,2′-biphenol linkage are reported. Highly efficient kinetic resolution of the monomeric tetrahydroxanthone core structures was achieved using homobenzotetramisole catalysis. DMA=N,N-dimethyl acetamide, MOM=methoxymethyl.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3107-3110 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 53 |
| Issue number | 12 |
| DOIs | |
| State | Published - Mar 17 2014 |
| Externally published | Yes |
Keywords
- dimerization
- kinetic resolution
- natural products
- stannanes
- total synthesis
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)