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Total Synthesis of Dimeric HPI Alkaloids |
| Xianfu Shen, Yongyun Zhou, Yongkai Xi, Jingfeng Zhao, Hongbin Zhang |
| Key Laboratory of Medicinal Chemistry for Natural Resource(Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China |
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Abstract In this paper, we report a full account of the synthesis of dimeric hexahydropyrroloindole alkaloids and its analogues. The key feature of our new strategy is the novel catalytic copper (10%) mediated intramolecular arylations of o-haloanilides followed by intermolecular oxidative dimerization of the resulting oxindoles in one pot. This sequential reaction leads to the key intermediates for the synthesis of (+)-chimonanthine, (+)-folicanthine, (-)-calycanthine and (-)-ditryptophenaline. Graphical Abstract In the presence of catalytic amount of cuprous iodide (10%), an intramolecular arylation of ohaloanilidesfollowedby an intermolecularoxidative dimerizationof the resultingoxindolesleads to a commonintermediatefor the synthesis of (+)-chimonanthine, (+)-folicanthine and (-)-calycanthine. Based on this cascade sequence, we also developed a flexible strategy towards the asymmetric syntheses of dimeric HPI alkaloids (-)-ditryptophenaline and its analogues.
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| Keywords
Copper catalyzed reaction
Oxidative dimerization
Total synthesis
Hexahydropyrroloindole
Alkaloids
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| Fund:This work was supported by Grants from Natural Science Foundation of China (20925205 and 21332007);the Program for Changjiang Scholars and Innovative Research Team in University (IRT13095);Yunnan Provincial Science and Technology Department (2010GA014) and the Program for Yunling Scholars.Dr.Xiaonian Li of the Kunming Institute of Botany is gratefully acknowledged for X-ray crystallographic analysis of compound 23.CCDC 1409209(23) |
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Issue Date: 08 February 2018
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