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

Publisher： John Wiley & Sons Inc

E-ISSN： 1521-3773|55|38|11656-11659

ISSN： 1433-7851

Source： ANGEWANDTE CHEMIE INTERNATIONAL EDITION, Vol.55, Iss.38, 2016-09, pp. : 11656-11659

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Abstract

AbstractThe 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.

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