Details
| Original language | English |
|---|---|
| Pages (from-to) | 11656-11659 |
| Number of pages | 4 |
| Journal | Angewandte Chemie - International Edition |
| Volume | 55 |
| Issue number | 38 |
| Publication status | Published - 12 Sept 2016 |
| Externally published | Yes |
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.
Keywords
- alpha-ketol rearrangement, Alzheimer's disease, C-H activation, strophasterolA, total synthesis, C–H activation, α-ketol rearrangement, strophasterol A
ASJC Scopus subject areas
- Chemistry(all)
- General Chemistry
- Chemical Engineering(all)
- Catalysis
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In: Angewandte Chemie - International Edition, Vol. 55, No. 38, 12.09.2016, p. 11656-11659.
Research output: Contribution to journal › Article › Research › 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 -