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A New Approach to Pyrrolocoumarin Derivatives by Palladium‐Catalyzed Reactions: Expedient Construction of Polycyclic Lamellarin Scaffold
Author(s) -
Chen Lei,
Xu MingHua
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900287
Subject(s) - hydroamination , chemistry , intramolecular force , palladium , scaffold , catalysis , pyrrole , combinatorial chemistry , ring (chemistry) , stereochemistry , organic chemistry , database , computer science
A new and efficient protocol for straightforward synthesis of chromeno[3,4‐ b ]pyrrol‐4(3 H )‐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(3 H )‐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.