title: Synthesis of Strophasterol A 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.
authors.affiliation: Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195, Berlin, Germany.
authors.forename: Robert C
authors.identifier: 0000-0002-3431-816X
authors.initials: RC
authors.lastname: Heinze
authors.affiliation: Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195, Berlin, Germany.
authors.forename: Dieter
authors.identifier: 0000-0002-0583-7024
authors.initials: D
authors.lastname: Lentz
authors.affiliation: Institute of Chemistry and Biochemistry, Freie Universität Berlin, Takustraße 3, 14195, Berlin, Germany. philipp.heretsch@fu-berlin.de.
authors.forename: Philipp
authors.identifier: 0000-0002-9967-3541
authors.initials: P
authors.lastname: Heretsch
mesh_terms: D000363:Agaricales / Q000737:chemistry / Q000378:metabolism; D001688:Biological Products / Q000737:chemistry / Q000378:metabolism; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D012632:Secosteroids / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001688:Biological Products; D012632:Secosteroids
keywords: Alzheimer's disease; C-H activation; strophasterol A; total synthesis; α-ketol rearrangement