Details
| Original language | English |
|---|---|
| Pages (from-to) | 9971-9981 |
| Number of pages | 11 |
| Journal | Chemistry - A European Journal |
| Volume | 26 |
| Issue number | 44 |
| Early online date | 21 Apr 2020 |
| Publication status | Published - 7 Aug 2020 |
| Externally published | Yes |
Abstract
In this work, a full account of the authors’ synthetic studies is reported that culminated in the first synthesis of 13(14→8),14(8→7)diabeo-steroid swinhoeisterol A as well as the related dankasterones A and B, 13(14→8)abeo-steroids, and periconiastone A, a 13(14→8)abeo-4,14-cyclo-steroid. Experiments are described in detail that provided further insight into the mechanism of the switchable radical framework reconstruction approach. By discussing failed strategies and tactics towards swinhoeisterol A, the successful route that also allowed an access to structurally closely related analogues, such as Δ 22-24-epi-swinhoeisterol A, is eventually presented.
Keywords
- biomimetic synthesis, natural product synthesis, radical reactions, rearrangement, steroids
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - A European Journal, Vol. 26, No. 44, 07.08.2020, p. 9971-9981.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Discoveries and Challenges en Route to Swinhoeisterol A
AU - Duecker, Fenja L.
AU - Heinze, Robert C.
AU - Steinhauer, Simon
AU - Heretsch, Philipp
N1 - Funding Information: Financial support for this work was provided by Deutsche Forschungsgemeinschaft (Grant No. HE 7133/7‐1), the Boehringer Ingelheim Stiftung (exploration grant to P.H.), and Studienstiftung des Deutschen Volkes (Ph.D. scholarship to R.C.H.). We acknowledge the assistance of the Core Facility BioSupraMol supported by the DFG.
PY - 2020/8/7
Y1 - 2020/8/7
N2 - In this work, a full account of the authors’ synthetic studies is reported that culminated in the first synthesis of 13(14→8),14(8→7)diabeo-steroid swinhoeisterol A as well as the related dankasterones A and B, 13(14→8)abeo-steroids, and periconiastone A, a 13(14→8)abeo-4,14-cyclo-steroid. Experiments are described in detail that provided further insight into the mechanism of the switchable radical framework reconstruction approach. By discussing failed strategies and tactics towards swinhoeisterol A, the successful route that also allowed an access to structurally closely related analogues, such as Δ 22-24-epi-swinhoeisterol A, is eventually presented.
AB - In this work, a full account of the authors’ synthetic studies is reported that culminated in the first synthesis of 13(14→8),14(8→7)diabeo-steroid swinhoeisterol A as well as the related dankasterones A and B, 13(14→8)abeo-steroids, and periconiastone A, a 13(14→8)abeo-4,14-cyclo-steroid. Experiments are described in detail that provided further insight into the mechanism of the switchable radical framework reconstruction approach. By discussing failed strategies and tactics towards swinhoeisterol A, the successful route that also allowed an access to structurally closely related analogues, such as Δ 22-24-epi-swinhoeisterol A, is eventually presented.
KW - biomimetic synthesis
KW - natural product synthesis
KW - radical reactions
KW - rearrangement
KW - steroids
UR - http://www.scopus.com/inward/record.url?scp=85087213162&partnerID=8YFLogxK
U2 - 10.1002/chem.202001405
DO - 10.1002/chem.202001405
M3 - Article
VL - 26
SP - 9971
EP - 9981
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 44
ER -