Total Synthesis of Acanthodoral Using a Rearrangement Strategy

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

doi:10.1021/acs.orglett.3c03717

Total Synthesis of Acanthodoral Using a Rearrangement Strategy

Alina Eggert
, Karl T. Schuppe
, Hazel L.S. Fuchs
, Mark Brönstrup
, Markus Kalesse^*

^*Corresponding author for this work

Institute of Organic Chemistry

Helmholtz Centre for Infection Research (HZI)

Research output: Contribution to journal › Article › Research › peer review

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.

Original language	English
Pages (from-to)	2893-2896
Number of pages	4
Journal	Organic letters
Volume	26
Issue number	15
E-pub ahead of print	2 Jan 2024
DOIs	https://doi.org/10.1021/acs.orglett.3c03717
Publication status	Published - 19 Apr 2024

UN Sustainable Development Goals (SDGs)

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.3c03717Licence: CC BY 4.0

Cite this

@article{1abe14f9173843d984fd0da3e7ec9642,

title = "Total Synthesis of Acanthodoral Using a Rearrangement Strategy",

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.",

author = "Alina Eggert and Schuppe, \{Karl T.\} and Fuchs, \{Hazel L.S.\} and Mark Br{\"o}nstrup and Markus Kalesse",

year = "2024",

month = apr,

day = "19",

doi = "10.1021/acs.orglett.3c03717",

language = "English",

volume = "26",

pages = "2893--2896",

journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

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 - https://www.scopus.com/pages/publications/85181831280

U2 - 10.1021/acs.orglett.3c03717

DO - 10.1021/acs.orglett.3c03717

M3 - Article

AN - SCOPUS:85181831280

SN - 1523-7060

VL - 26

SP - 2893

EP - 2896

JO - Organic letters

JF - Organic letters

IS - 15

ER -

Total Synthesis of Acanthodoral Using a Rearrangement Strategy

Abstract

UN Sustainable Development Goals (SDGs)

ASJC Scopus subject areas

Access to Document

Other files and links

The total synthesis of acanthodoral and studies on the total synthesis of waihoensene and the asymmetric bisvinylogous Mukaiyama aldol reaction

Cite this