期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 10, 期 30, 页码 6010-6021出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob25115a
关键词
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资金
- Australian Research Council [DP110100112, DP0985623]
- ARC Centre of Excellence for Free Radical Chemistry and Biotechnology
- Australian Research Council [DP0985623] Funding Source: Australian Research Council
The methyl ether derivatives 2, 4 and 6 of the mulberry Diels-Alder adducts chalcomoracin (1) and mulberrofuran C (3) and kuwanon J (5) respectively have been synthesized by a thermal [4 + 2]-cycloaddition reaction between a chalcone and dehydroprenyl diene. A H-bonded ortho OH substituent on the chalcone was found to be essential for Diels-Alder reactivity. Density functional theory calculations show that the OH group lowers the barrier for the Diels-Alder reaction by 2-3 kcal mol(-1) compared with OMe. The acceleration by the OH group is traced to two transition-state effects: a stronger diene-chalcone interaction and better planarity of the aryl-diene unit.
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