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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Total synthesis and determination of the absolute configuration of (+)-omaezakianol
Yoshiki Morimoto1, Tatsuya Okita, Hitomi Kambara
1Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan. morimoto@sci.osaka-cu.ac.jp
Abstract:
The proof of the pudding: The first asymmetric total synthesis of the marine tetracyclic oxasqualenoid (+)-omaezakianol features a convergent olefin cross-metathesis between a monotetrahydrofuran fragment and a triepoxy alkene, and cascade oxacyclizations of a triepoxy alcohol to form the right-hand three ether rings. The total synthesis proved the absolute configuration of (+)-omaezakianol to be that shown.
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