Total Synthesis of Crocagin A

Filip Bihelovic, Desiree Stichnoth, Frank Surup, Rolf Müller, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Crocagin A (1) combines an attractive molecular structure with an unusual biosynthesis and bioactivity. An efficient synthesis of crocagin A is presented that hinges on an early formation of the heterotricyclic core, an electrophilic amination, and the stereoselective hydrogenation of a tetrasubstituted double bond. This synthesis confirms the absolute configuration of crocagin A and provides access to the natural product and derivatives thereof for further biological testing.

Original languageEnglish (US)
Pages (from-to)12848-12851
Number of pages4
JournalAngewandte Chemie - International Edition
Volume56
Issue number42
DOIs
StatePublished - Oct 9 2017

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Amination
Biosynthesis
Hinges
Bioactivity
Biological Products
Molecular structure
Hydrogenation
Derivatives
Testing

Keywords

  • electrophilic amination
  • hydrogenation
  • natural products
  • RiPPs
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Bihelovic, F., Stichnoth, D., Surup, F., Müller, R., & Trauner, D. (2017). Total Synthesis of Crocagin A. Angewandte Chemie - International Edition, 56(42), 12848-12851. https://doi.org/10.1002/anie.201612641

Total Synthesis of Crocagin A. / Bihelovic, Filip; Stichnoth, Desiree; Surup, Frank; Müller, Rolf; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 56, No. 42, 09.10.2017, p. 12848-12851.

Research output: Contribution to journalArticle

Bihelovic, F, Stichnoth, D, Surup, F, Müller, R & Trauner, D 2017, 'Total Synthesis of Crocagin A', Angewandte Chemie - International Edition, vol. 56, no. 42, pp. 12848-12851. https://doi.org/10.1002/anie.201612641
Bihelovic F, Stichnoth D, Surup F, Müller R, Trauner D. Total Synthesis of Crocagin A. Angewandte Chemie - International Edition. 2017 Oct 9;56(42):12848-12851. https://doi.org/10.1002/anie.201612641
Bihelovic, Filip ; Stichnoth, Desiree ; Surup, Frank ; Müller, Rolf ; Trauner, Dirk. / Total Synthesis of Crocagin A. In: Angewandte Chemie - International Edition. 2017 ; Vol. 56, No. 42. pp. 12848-12851.
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