Total Synthesis of Acanthodoral Using a Rearrangement Strategy

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Authors

  • Alina Eggert
  • Karl T. Schuppe
  • Hazel L.S. Fuchs
  • Mark Brönstrup
  • Markus Kalesse

Research Organisations

External Research Organisations

  • Helmholtz Centre for Infection Research (HZI)
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Details

Original languageEnglish
Pages (from-to)2893-2896
Number of pages4
JournalOrganic letters
Volume26
Issue number15
Early online date2 Jan 2024
Publication statusPublished - 19 Apr 2024

Abstract

We present the second total synthesis of (±)-acanthodoral, a sesquiterpenoid derived from the marine nudibranch Acanthodoris nanaimoensis. Our approach involves a concise three-step transformation from a previously reported compound, resulting in the formation of a less strained precursor of the bicyclo[3.1.1]heptane core and both all-carbon quaternary stereocenters characteristic of the natural product. Notably, this synthetic route incorporates two pivotal steps: a Sm(II)-induced 1,2-rearrangement and a semipinacol rearrangement.

ASJC Scopus subject areas

Sustainable Development Goals

Cite this

Total Synthesis of Acanthodoral Using a Rearrangement Strategy. / Eggert, Alina; Schuppe, Karl T.; Fuchs, Hazel L.S. et al.
In: Organic letters, Vol. 26, No. 15, 19.04.2024, p. 2893-2896.

Research output: Contribution to journalArticleResearchpeer review

Eggert, A, Schuppe, KT, Fuchs, HLS, Brönstrup, M & Kalesse, M 2024, 'Total Synthesis of Acanthodoral Using a Rearrangement Strategy', Organic letters, vol. 26, no. 15, pp. 2893-2896. https://doi.org/10.1021/acs.orglett.3c03717
Eggert, A., Schuppe, K. T., Fuchs, H. L. S., Brönstrup, M., & Kalesse, M. (2024). Total Synthesis of Acanthodoral Using a Rearrangement Strategy. Organic letters, 26(15), 2893-2896. https://doi.org/10.1021/acs.orglett.3c03717
Eggert A, Schuppe KT, Fuchs HLS, Brönstrup M, Kalesse M. Total Synthesis of Acanthodoral Using a Rearrangement Strategy. Organic letters. 2024 Apr 19;26(15):2893-2896. Epub 2024 Jan 2. doi: 10.1021/acs.orglett.3c03717
Eggert, Alina ; Schuppe, Karl T. ; Fuchs, Hazel L.S. et al. / Total Synthesis of Acanthodoral Using a Rearrangement Strategy. In: Organic letters. 2024 ; Vol. 26, No. 15. pp. 2893-2896.
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