Total Synthesis of Acanthodoral Using a Rearrangement Strategy
- authored by
- Alina Eggert, Karl T. Schuppe, Hazel L.S. Fuchs, Mark Brönstrup, Markus Kalesse
- 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.
- Organisation(s)
-
Institute of Organic Chemistry
- External Organisation(s)
-
Helmholtz Centre for Infection Research (HZI)
- Type
- Article
- Journal
- Organic letters
- Volume
- 26
- Pages
- 2893-2896
- No. of pages
- 4
- ISSN
- 1523-7060
- Publication date
- 19.04.2024
- Publication status
- Published
- Peer reviewed
- Yes
- ASJC Scopus subject areas
- Biochemistry, Physical and Theoretical Chemistry, Organic Chemistry
- Sustainable Development Goals
- SDG 14 - Life Below Water
- Electronic version(s)
-
https://doi.org/10.1021/acs.orglett.3c03717 (Access:
Open)
