Abstract
A merged conjugate addition/oxidative coupling sequence that represents an efficient strategy for preparing structurally diverse pyrroles has been developed. Success of the method hinged upon the controlled oxidative coupling of unsymmetrical silyl bis-enol ether intermediates, formed by the 1,4-addition of a Grignard reagent with subsequent enolate trapping by a (chloro)silylenol ether. The process was applied to the first enantioselective syntheses of the biologically active pyrrolophane natural products, metacycloprodigiosin and prodigiosin R1.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 14579-14583 |
| Number of pages | 5 |
| Journal | Journal of the American Chemical Society |
| Volume | 131 |
| Issue number | 40 |
| DOIs | |
| State | Published - Oct 14 2009 |
Funding
ASJC Scopus subject areas
- General Chemistry
- Biochemistry
- Catalysis
- Colloid and Surface Chemistry