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 -