24. Synthesis of Strophasterol A Guided by a Proposed Biosynthesis and Innate Reactivity

R.C. Heinze, D. Lentz, P. Heretsch— 2016

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.

Title24. Synthesis of Strophasterol A Guided by a Proposed Biosynthesis and Innate Reactivity
AuthorR.C. Heinze, D. Lentz, P. Heretsch
Date2016
IdentifierDOI: 10.1002/anie.201605752
Source(s)
CitationAngew. Chem. Int. Ed. 2016, 55, 11656-11659; Angew. Chem. 2016, 128, 11828-11831