Unexpected diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin

Takahiro Suzuki, Yuria Miyajima, Kaname Suzuki, Kanako Iwakiri, Masaki Koshimizu, Go Hirai, Mikiko Sodeoka, Susumu Kobayashi

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20 Citations (Scopus)

Abstract

The biomimetic synthesis of the advanced model compound of chloropupukeananin has been achieved. The present synthesis features an unexpected enantiomer-differentiating Diels-Alder/carbonyl-ene cascade under high-pressure conditions and a base-promoted migration of the salicyl group.

Original languageEnglish
Pages (from-to)1748-1751
Number of pages4
JournalOrganic Letters
Volume15
Issue number7
DOIs
Publication statusPublished - Apr 5 2013
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Suzuki, T., Miyajima, Y., Suzuki, K., Iwakiri, K., Koshimizu, M., Hirai, G., ... Kobayashi, S. (2013). Unexpected diels-Alder/carbonyl-ene cascade toward the biomimetic synthesis of chloropupukeananin. Organic Letters, 15(7), 1748-1751. https://doi.org/10.1021/ol400549q