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Updated: Jul 10, 2026
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Vinigrol: a compact, diene-transmissive Diels-Alder strategy to the tricyclic core
Michael Santos Souweha1, Gary D Enright, Alex G Fallis
1Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5.
Abstract:
A short (six steps from 17), versatile route to the tricyclic core of Vinigrol is described. A Lewis acid catalyzed and self-assembled Diels-Alder (LACASA-DA) reaction from the homoallylic cross-conjugated trienol 15 with N-methylmaleimide afforded the monoadduct 17 with diastereo-, regio-, and chemoselective control. Oxidation and installation of an acetylene (Ohira's reagent) followed by further manipulations afforded trienone 24. The second intramolecular Diels-Alder (at 45 degrees C) reaction assembled the tricyclic skeleton 25 directly. The configuration of 25 was confirmed by X-ray analysis.
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