Metal-Free Synthetic Shortcut to Octahydro-Dipyrroloquinoline Skeletons from 2,5-Cyclohexadienone Derivatives and l‑Proline

The tandem decarboxylative condensation–dimerization reaction of l-proline with 2,5-cyclohexadienones including p-quinone monoacetals, p-quinol ethers, and p-quinols is reported to provide a concise and rapid synthesis of octahydro-dipyrroloquinoline compounds. The reaction features the use of cost-...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-08, Vol.86 (15), p.10397-10406
Main Authors: Zhang, Can, Li, Jianbin, Wang, Xin, Shen, Xuan, Zhu, Dunru, Shen, Ruwei
Format: Article
Language:English
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Summary:The tandem decarboxylative condensation–dimerization reaction of l-proline with 2,5-cyclohexadienones including p-quinone monoacetals, p-quinol ethers, and p-quinols is reported to provide a concise and rapid synthesis of octahydro-dipyrroloquinoline compounds. The reaction features the use of cost-effective and readily available starting materials, high efficiency, metal-free and green reaction conditions. The reaction is applied to the synthesis of incargranine B aglycone. The discovery of this reaction may suggest a biosynthetic pathway from 2,5-cyclohexadienones and proline for natural ingredients containing pyrroloquinoline moieties.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01083