Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 11656-11659 |
| Seitenumfang | 4 |
| Fachzeitschrift | Angewandte Chemie - International Edition |
| Jahrgang | 55 |
| Ausgabenummer | 38 |
| Publikationsstatus | Veröffentlicht - 12 Sept. 2016 |
| Extern publiziert | Ja |
Abstract
The synthesis of strophasterol A, a moderator of endoplasmatic reticulum (ER) stress in Alzheimer's disease, and the first member of a structurally unprecedented class of secosterols, was achieved through the implementation of a key step of its proposed biosynthesis and two C−H oxidations. Analysis of the innate reactivity of the intermediates enabled the identification of a novel way to prepare an α-chloro-γ-hydroxy-δ-keto enone, as well as its vinylogous α-ketol rearrangement to a δ-keto carboxylic acid.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Chemische Verfahrenstechnik (insg.)
- Katalyse
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in: Angewandte Chemie - International Edition, Jahrgang 55, Nr. 38, 12.09.2016, S. 11656-11659.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Synthesis of StrophasterolA Guided by a Proposed Biosynthesis and Innate Reactivity
AU - Heinze, Robert C.
AU - Lentz, Dieter
AU - Heretsch, Philipp
N1 - Publisher Copyright: © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2016/9/12
Y1 - 2016/9/12
N2 - The synthesis of strophasterol A, a moderator of endoplasmatic reticulum (ER) stress in Alzheimer's disease, and the first member of a structurally unprecedented class of secosterols, was achieved through the implementation of a key step of its proposed biosynthesis and two C−H oxidations. Analysis of the innate reactivity of the intermediates enabled the identification of a novel way to prepare an α-chloro-γ-hydroxy-δ-keto enone, as well as its vinylogous α-ketol rearrangement to a δ-keto carboxylic acid.
AB - The synthesis of strophasterol A, a moderator of endoplasmatic reticulum (ER) stress in Alzheimer's disease, and the first member of a structurally unprecedented class of secosterols, was achieved through the implementation of a key step of its proposed biosynthesis and two C−H oxidations. Analysis of the innate reactivity of the intermediates enabled the identification of a novel way to prepare an α-chloro-γ-hydroxy-δ-keto enone, as well as its vinylogous α-ketol rearrangement to a δ-keto carboxylic acid.
KW - alpha-ketol rearrangement
KW - Alzheimer's disease
KW - C-H activation
KW - strophasterolA
KW - total synthesis
KW - C–H activation
KW - α-ketol rearrangement
KW - strophasterol A
UR - http://www.scopus.com/inward/record.url?scp=84981745175&partnerID=8YFLogxK
U2 - 10.1002/anie.201605752
DO - 10.1002/anie.201605752
M3 - Article
VL - 55
SP - 11656
EP - 11659
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
SN - 1433-7851
IS - 38
ER -