Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 351, Issue 11-12, Pages 2005-2012Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200900287
Keywords
coumarin derivatives; cross-coupling; hydroamination; lamellarin; palladium
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Funding
- National Natural Science Foundation of China [20721003]
- Shanghai Rising-Star Program [08QH14027]
- Chinese Academy of Sciences
- Shanghai Institute of Materia Medica
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A new and efficient protocol for straightforward synthesis of chromeno[3,4-b]pyrrol-4(3H)-one derivatives by palladium-catalyzed sequential coupling/cyclization reactions has been developed. The key strategy relies on creation of pyrrole ring through palladium-catalyzed intramolecular hydroamination of related acetylenic aminocoumarins. The synthetic utility of the obtained chromeno[3,4-b]pyrrol-4(3H)-one product has been demonstrated by the expedient synthesis of polycyclic lamellarin scaffold in four steps. It provides a new entry to synthesis of potentially valuable lamellarin analogues.
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