Premium
Synthesis of Strophasterol A Guided by a Proposed Biosynthesis and Innate Reactivity
Author(s) -
Heinze Robert C.,
Lentz Dieter,
Heretsch Philipp
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605752
Subject(s) - reactivity (psychology) , biosynthesis , moderation , chemistry , identification (biology) , stereochemistry , endoplasmic reticulum , combinatorial chemistry , biochemistry , biology , medicine , psychology , enzyme , botany , social psychology , alternative medicine , pathology
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.