Abstract
A short and efficient total synthesis of naturally occurring carbazole clauraila A (1) is described. The approach is designed on the basis of the key regioselective Diels-Alder reaction of the properly substituted exo-2-oxazolidinone diene 3 with acrolein (4) to give the corresponding adduct 2. The latter is converted to functionalised diarylamine 8, which is cyclised to the desired carbazole 1 through a Pd-promoted or -catalysed double C-H bond activation process in a fairly good overall yield.
Original language | English |
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Pages (from-to) | 1749-1756 |
Number of pages | 8 |
Journal | Natural Product Research |
Volume | 27 |
Issue number | 19 |
DOIs | |
State | Published - 1 Oct 2013 |
Keywords
- 1-methoxycarbazoles
- 4,5-dimethylene-2-oxazolidinone dienes
- CZH bond activation
- Pd(II) cyclisation
- clauraila A