AI Article Synopsis
- The synthesis of 3-(3a-indolyl)hexahydropyrroloindoline motifs is crucial for creating various alkaloid compounds.
- An innovative intermolecular asymmetric cascade dearomatization reaction has been developed using indole acetamides combined with 3-indolylphenyliodonium salts.
- This method allows for efficient production of compounds with a unique carbon quaternary stereocenter and has been successfully applied in the asymmetric synthesis of folicanthine.
Article Abstract
The rapid and direct asymmetric synthesis of 3-(3a-indolyl)hexahydropyrroloindoline motifs is an extremely important part of the total synthesis of several alkaloid structures. Herein, an intermolecular, asymmetric cascade dearomatization reaction of indole acetamides with 3-indolylphenyliodonium salts has been developed. This protocol provides a straightforward access to 3-(3a-indolyl)hexahydropyrroloindolines bearing an all-carbon quaternary stereocenter at the C3 position of the indoline ring with high enantioselectivities. The utility of the protocol has been demonstrated by the formal asymmetric synthesis of folicanthine.
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| http://dx.doi.org/10.1002/chem.201602229 | DOI Listing |
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