Expedient synthesis of (+)-lycopalhine A

Benjamin M. Williams, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Two amino acids play a key role in the first total synthesis of lycopalhine A. l-glutamic acid serves as a convenient chiral starting material for the 13-step synthesis, and l-proline promotes an unusual 5-endo-trig Mannich cyclization that generates the central pyrrolidine ring of the Lycopodium alkaloid. The bicyclo[3.3.0]octanol moiety of the molecule is formed through an intramolecular aldol addition that may occur spontaneously in nature. Just Another Mannich Monday: By using l-glutamate and l-proline as a starting material and catalyst, respectively, the complex alkaloid lycopalhine A was assembled in only 13 steps. The synthesis features not only an unusual Mannich reaction but also a biomimetic aldol addition that completes the intricate carbon skeleton of the natural product.

Original languageEnglish (US)
Pages (from-to)2191-2194
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number6
DOIs
StatePublished - Feb 5 2016

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Alkaloids
Proline
Glutamic Acid
Octanols
Cyclization
Biomimetics
Biological Products
Amino acids
Carbon
Amino Acids
Catalysts
Molecules
Acids
3-hydroxybutanal
pyrrolidine

Keywords

  • aldol reaction
  • amino acids
  • Lycopodium alkaloids
  • Mannich reaction
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Expedient synthesis of (+)-lycopalhine A. / Williams, Benjamin M.; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 55, No. 6, 05.02.2016, p. 2191-2194.

Research output: Contribution to journalArticle

Williams, Benjamin M. ; Trauner, Dirk. / Expedient synthesis of (+)-lycopalhine A. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 6. pp. 2191-2194.
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