Abstract
A total synthesis of the marine natural product diazonamide A (1) has been accomplished. This work features a highly stereoselective synthesis of the C(10) quaternary center and the central furanoindoline core enabled by an iminium-catalyzed alkylation-cyclization cascade. Additionally, a magnesium-mediated intramolecular macroaldolization and a palladium-catalyzed tandem borylation/annulation were developed to enable the closure of the two 12-membered macrocycles of diazonamide A. This synthesis involves 20 steps in its longest linear sequence and proceeds in 1.8% overall yield.
Original language | English (US) |
---|---|
Pages (from-to) | 308-311 |
Number of pages | 4 |
Journal | Chemical Science |
Volume | 2 |
Issue number | 2 |
DOIs | |
State | Published - 2011 |
All Science Journal Classification (ASJC) codes
- General Chemistry