Biomimetic Total Synthesis of Santalin Y

Sebastian Strych, Guillaume Journot, Ryan P. Pemberton, Selina C. Wang, Dean J. Tantillo, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

A biomimetic total synthesis of santalin Y, a structurally complex but racemic natural product, is described. The key step is proposed to be a (3+2) cycloaddition of a benzylstyrene to a "vinylogous oxidopyrylium", which is followed by an intramolecular Friedel-Crafts reaction. This cascade generates the unique oxafenestrane framework of the target molecule and sets its five stereocenters in one operation. Our work provides rapid access to santalin Y and clarifies its biosynthetic relationship with other colorants isolated from red sandalwood.

Original languageEnglish (US)
Pages (from-to)5079-5083
Number of pages5
JournalAngewandte Chemie - International Edition
Volume54
Issue number17
DOIs
StatePublished - Apr 20 2015

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Friedel-Crafts reaction
Cycloaddition
Biomimetics
Molecules
Biological Products
santalin Y

Keywords

  • biomimetic synthesis
  • dipolar cycloaddition
  • polyphenols
  • racemic natural products
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Strych, S., Journot, G., Pemberton, R. P., Wang, S. C., Tantillo, D. J., & Trauner, D. (2015). Biomimetic Total Synthesis of Santalin Y. Angewandte Chemie - International Edition, 54(17), 5079-5083. https://doi.org/10.1002/anie.201411350

Biomimetic Total Synthesis of Santalin Y. / Strych, Sebastian; Journot, Guillaume; Pemberton, Ryan P.; Wang, Selina C.; Tantillo, Dean J.; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 54, No. 17, 20.04.2015, p. 5079-5083.

Research output: Contribution to journalArticle

Strych, S, Journot, G, Pemberton, RP, Wang, SC, Tantillo, DJ & Trauner, D 2015, 'Biomimetic Total Synthesis of Santalin Y', Angewandte Chemie - International Edition, vol. 54, no. 17, pp. 5079-5083. https://doi.org/10.1002/anie.201411350
Strych S, Journot G, Pemberton RP, Wang SC, Tantillo DJ, Trauner D. Biomimetic Total Synthesis of Santalin Y. Angewandte Chemie - International Edition. 2015 Apr 20;54(17):5079-5083. https://doi.org/10.1002/anie.201411350
Strych, Sebastian ; Journot, Guillaume ; Pemberton, Ryan P. ; Wang, Selina C. ; Tantillo, Dean J. ; Trauner, Dirk. / Biomimetic Total Synthesis of Santalin Y. In: Angewandte Chemie - International Edition. 2015 ; Vol. 54, No. 17. pp. 5079-5083.
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