Biomimetic Synthesis of (+)-Aspergillin PZ

Julius R. Reyes, Nils Winter, Lukas Spessert, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

The cytochalasans are a large family of polyketide natural products with potent bioactivities. Amongst them, the aspochalasins show particularly intricate and fascinating structures. To gain insight into their structural diversity and innate reactivity, we have developed a rapid synthesis of aspochalasin D, the central member of the family. It proceeded in 13 steps starting from divinyl carbinol and utilized a high pressure Diels–Alder reaction that features high regio- and stereoselectivity. So far, our work has culminated in a biomimetic synthesis of aspergillin PZ, an intricate pentacyclic aspochalasan.

Original languageEnglish (US)
Pages (from-to)15587-15591
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number47
DOIs
StatePublished - Nov 19 2018

Fingerprint

Biomimetics
Polyketides
Stereoselectivity
Regioselectivity
Bioactivity
Biological Products
Methanol
aspergillin PZ
aspochalasin D
1,3-butadiene

Keywords

  • biomimetic synthesis
  • cytochalasans
  • Diels–Alder cycloaddition
  • high-pressure chemistry
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Reyes, J. R., Winter, N., Spessert, L., & Trauner, D. (2018). Biomimetic Synthesis of (+)-Aspergillin PZ. Angewandte Chemie - International Edition, 57(47), 15587-15591. https://doi.org/10.1002/anie.201809703

Biomimetic Synthesis of (+)-Aspergillin PZ. / Reyes, Julius R.; Winter, Nils; Spessert, Lukas; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 57, No. 47, 19.11.2018, p. 15587-15591.

Research output: Contribution to journalArticle

Reyes, JR, Winter, N, Spessert, L & Trauner, D 2018, 'Biomimetic Synthesis of (+)-Aspergillin PZ', Angewandte Chemie - International Edition, vol. 57, no. 47, pp. 15587-15591. https://doi.org/10.1002/anie.201809703
Reyes, Julius R. ; Winter, Nils ; Spessert, Lukas ; Trauner, Dirk. / Biomimetic Synthesis of (+)-Aspergillin PZ. In: Angewandte Chemie - International Edition. 2018 ; Vol. 57, No. 47. pp. 15587-15591.
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