Synthesis of StrophasterolA Guided by a Proposed Biosynthesis and Innate Reactivity

Research output: Contribution to journalArticleResearchpeer review

Authors

External Research Organisations

  • Freie Universität Berlin (FU Berlin)
View graph of relations

Details

Original languageEnglish
Pages (from-to)11656-11659
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number38
Publication statusPublished - 12 Sept 2016
Externally publishedYes

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

Cite this

Synthesis of StrophasterolA Guided by a Proposed Biosynthesis and Innate Reactivity. / Heinze, Robert C.; Lentz, Dieter; Heretsch, Philipp.
In: Angewandte Chemie - International Edition, Vol. 55, No. 38, 12.09.2016, p. 11656-11659.

Research output: Contribution to journalArticleResearchpeer review

Download
@article{ab3b18a096cf4a2da46493a6943bbf3c,
title = "Synthesis of StrophasterolA Guided by a Proposed Biosynthesis and Innate Reactivity",
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",
author = "Heinze, {Robert C.} and Dieter Lentz and Philipp Heretsch",
note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",
year = "2016",
month = sep,
day = "12",
doi = "10.1002/anie.201605752",
language = "English",
volume = "55",
pages = "11656--11659",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "38",

}

Download

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 -

By the same author(s)