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- W1999348565 abstract "An asymmetric synthesis of the quinone epoxide dimer (+)-torreyanic acid (48) has been accomplished employing [4 + 2] dimerization of diastereomeric 2H-pyran monomers. Synthesis of the related monomeric natural product (+)-ambuic acid (2) has also been achieved which establishes the biosynthetic relationship between these two natural products. A tartrate-mediated nucleophilic epoxidation involving hydroxyl group direction facilitated the asymmetric synthesis of a key chiral quinone monoepoxide intermediate. Thermolysis experiments have also been conducted on a model dimer based on the torreyanic acid core structure and facile retro Diels-Alder reaction processes and equilibration of diastereomeric 2H-pyrans have been observed. Theoretical calculations of Diels-Alder transition states have been performed to evaluate alternative transition states for Diels-Alder dimerization of 2H-pyran quinone epoxide monomers and provide insight into the stereocontrol elements for these reactions." @default.
- W1999348565 created "2016-06-24" @default.
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- W1999348565 date "2003-04-01" @default.
- W1999348565 modified "2023-10-11" @default.
- W1999348565 title "Total Synthesis of the Quinone Epoxide Dimer (+)-Torreyanic Acid: Application of a Biomimetic Oxidation/Electrocyclization/Diels−Alder Dimerization Cascade<sup>1</sup>" @default.
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- W1999348565 doi "https://doi.org/10.1021/ja021396c" @default.
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