Polycyclic Indoles Made Easy

  • Author: Saskia Neubacher
  • Published Date: 03 November 2012
  • Source / Publisher: ChemistryOpen/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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Polycyclic indoles represent interesting structural motifs for biologically active molecules in medicinal chemistry. However, the preparation often requires extensive synthetic efforts and multistep approaches. Di-Han Zhang and Min Shi, Chinese Academy of Sciences, Shanghai, describe the usage of a binary catalytic system to achieve an efficient and highly regio- and stereoselective synthesis of polycyclic indoles starting out from isatin derivatives and allenic esters.

The sequential catalysis involves a gold-catalyzed rearrangement of a propargyl benzyl ether to the corresponding α,β-unsaturated ketone, and subsequently a [4+2] cycloaddition with an allenic ester to the desired polycyclic indole, catalyzed by a nitrogen-containing Lewis base. The synthesis requires very mild conditions, and a variety of substituents at different positions are tolerated, making this procedure an efficient entry to polycyclic indoles.

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