Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B

Joel F. Austin, Sung Gon Kim, Christopher J. Sinz, Wen Jing Xiao, David W.C. MacMillan

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Abstract

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 α,β-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 α,β-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.

Original languageEnglish (US)
Pages (from-to)5482-5487
Number of pages6
JournalProceedings of the National Academy of Sciences of the United States of America
Volume101
Issue number15
DOIs
StatePublished - Apr 13 2004

All Science Journal Classification (ASJC) codes

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