Total Synthesis and Assignment of the Absolute Configuration of (+)-Omphalic Acid
| Autor: | Dongsheng Qiu, Tao Zeng, Renzhi Chen, Yuhui Hua, Yujie Niu, Xin Lei, Yandong Zhang, Huayu Peng |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Cycloaddition Reaction
Molecular Structure Bicyclic molecule Stereochemistry Organic Chemistry Absolute configuration Total synthesis Stereoisomerism Octanes Ring (chemistry) Biochemistry Catalysis Cycloaddition Bridged Bicyclo Compounds chemistry.chemical_compound chemistry Aldol reaction Carboxylation Hydrogenation Diterpenes Physical and Theoretical Chemistry Octane |
| Zdroj: | Organic Letters. 23:6972-6976 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | Omphalane diterpenoids usually contain a cyclohexane-fused bicyclo[3.2.1]octane scaffold embedded with two continuous quaternary carbon centers, which pose considerable challenges to synthetic chemists. Herein, we reported the first total synthesis of omphalic acid with high stereochemical control, featuring an intermolecular Diels-Alder cycloaddition, ring reorganization through Criegee oxidative cleavage and programmed aldol condensations, conformationally controlled hydrogenation, and Pd-catalyzed carboxylation. The absolute configuration of omphalic acid was defined for the first time via the asymmetric total synthesis facilitated by a derivatization resolution protocol. |
| Databáze: | OpenAIRE |
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