Abstract
A novel and efficient synthesis of naturally occurring 1-methoxycarbazoles glycozolicine, mukolidine, and mukoline is developed by applying a regioselective Diels-Alder reaction of a 4,5-dimethyleneoxazolidin-2-one with acrolein. The cycloadduct is transformed to the corresponding functionalized diarylamine. The key palladium-catalyzed cyclization/deformylation cascade reaction of the latter leads to glycozolicine in high overall yield. Oxidation of the C6 methyl group provides the 6-formylcarbazole mukolidine, which is reduced to the respective natural alcohol mukoline.
Original language | English |
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Article number | M07910SS |
Pages (from-to) | 929-933 |
Number of pages | 5 |
Journal | Synthesis (Germany) |
Issue number | 6 |
DOIs | |
State | Published - 2011 |
Keywords
- 1-methoxycarbazoles
- 4,5-dimethyleneoxazolidin-2-one
- decarbonylation
- glycozolicine
- mukolidine
- mukoline
- palladium(II) cyclization