Journal
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
Volume 101, Issue 15, Pages 5482-5487Publisher
NATL ACAD SCIENCES
DOI: 10.1073/pnas.0308177101
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Funding
- NCI NIH HHS [F32 CA091635, 1-F32-CA91635-01] Funding Source: Medline
- NIGMS NIH HHS [R01 GM066142, R01 GM66142-01] Funding Source: Medline
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Pyrroloindoline and bispyrroloindoline are a subclass of alkaloid structural motifs that commonly exhibit biological activity. An enantioselective organocatalytic approach to the synthesis of pyrroloindoline architecture is described. The addition-cyclization of tryptamines with alpha,beta-unsaturated aldehydes in the presence of imidazolidinone catalysts 1 and 8 provides pyrroloindoline adducts in high yield and excellent enantioselectivities. This transformation is successful for a wide range of tryptamine and alpha,beta-unsaturated aldehyde substrates. This amine-catalyzed sequence has been extended to the enantioselective construction of furanoindoline frameworks. Application of this pyrroloindoline-forming reaction to natural product synthesis has been accomplished in the context of the enantioselective synthesis of (-)-flustramine B.
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