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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Formal Total Synthesis of Atropurpuran
Takahiro Suzuki1, Takeshi Koyama2, Kenta Nakanishi2
1Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, 060-0810 Hokkaido, Japan.
Abstract:
Atropurpuran, isolated from the roots of Aconitum hemsleyanum, is a non-alkaloidal diterpene which possesses a unique pentacyclic skeleton that contains an unprecedented tetracyclo[5.3.3.04,9.04,12]tridecane unit. We report herein the formal total synthesis of atropurpuran. The key features of our synthetic route are a high diastereoselective construction of the tri- and tetrasubstituted carbons (i.e., C4, C5, C10, and C20) through an Yb-catalyzed Mukaiyama aldol reaction in an aqueous medium and a one-pot operation including an intramolecular Diels-Alder reaction/ring-closing metathesis to construct the unique pentacyclic skeleton of atropurpuran.
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