Details
| Original language | English |
|---|---|
| Pages (from-to) | 2893-2896 |
| Number of pages | 4 |
| Journal | Organic letters |
| Volume | 26 |
| Issue number | 15 |
| Early online date | 2 Jan 2024 |
| Publication status | Published - 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
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
Sustainable Development Goals
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In: Organic letters, Vol. 26, No. 15, 19.04.2024, p. 2893-2896.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Total Synthesis of Acanthodoral Using a Rearrangement Strategy
AU - Eggert, Alina
AU - Schuppe, Karl T.
AU - Fuchs, Hazel L.S.
AU - Brönstrup, Mark
AU - Kalesse, Markus
PY - 2024/4/19
Y1 - 2024/4/19
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85181831280&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.3c03717
DO - 10.1021/acs.orglett.3c03717
M3 - Article
AN - SCOPUS:85181831280
VL - 26
SP - 2893
EP - 2896
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 15
ER -