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

• DOI: 10.1002/anie.201605752
• Publication Date: 2016-08-17T07:51:23Z
• Authors: Robert C. Heinze; Dieter Lentz; Philipp Heretsch
• Keywords: Reactivity; Moderation; Identification

Abstract The synthesis of strophasterol A, a moderator endoplasmatic reticulum (ER) stress in Alzheimer's disease, and the first member structurally unprecedented class secosterols, was achieved through implementation key step its proposed biosynthesis two C−H oxidations. Analysis innate reactivity intermediates enabled identification novel way to prepare an α‐chloro‐γ‐hydroxy‐δ‐keto enone, as well vinylogous α‐ketol rearrangement δ‐keto carboxylic acid.