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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Total Syntheses of Ganodilactone and Related Ganoderma-Derived Meroterpenoid Dimers via Intramolecular Vinylogous
Shogo Kamo1, Motoi Suzuki1, Kazuyuki Sugita1
1Department of Synthetic Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo, 142-8501, Japan.
Abstract:
Herein, we describe the first total syntheses of four Ganoderma-derived meroterpenoid dimers: ganodilactone, spirocochlealactone A, and dimercochlearlactones I and J. Highly substituted 5'H-spiro[chromane-4,2'-furan]-2,5'-dione core skeleton of these natural products was efficiently constructed through intramolecular vinylogous Michael addition reaction as a pivotal step. Starting from commercially available compounds, dimercochlearlactones I and J were synthesized with the longest linear sequence (LLS) of eight steps, whereas ganodilactone and spirocochlealactone A were synthesized with an LLS of 11 steps.
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