Abstract
The polycyclic ether class of marine natural products presents formidable and challenging synthetic targets due to their structural complexity and exceptionally potent biological activities. We have developed a highly convergent strategy for the assembly of a huge polycyclic ether array, which features Suzuki-Miyaura cross-coupling of alkylboranes, generated from exocyclic enol ethers, with cyclic ketene acetal triflates or phosphates combined with reductive ring-closure. The utility of this strategy was demonstrated by its application to synthetic studies on ciguatoxins, and the total syntheses of gambierol and gymnocin-A.
| Original language | English |
|---|---|
| Pages (from-to) | 1851-1874 |
| Number of pages | 24 |
| Journal | Synlett |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 2004 Sept 6 |
Keywords
- Cross-coupling
- Natural products
- Polycyclic ethers
- Suzuki-Miyaura reaction
- Total synthesis
ASJC Scopus subject areas
- Organic Chemistry
