Construction of Spirooxindole Skeleton Through Intramolecular Dieckmann Cyclization

doi:10.1007/s13659-017-0131-0

Natural Products and Bioprospecting ›› 2017, Vol. 7 ›› Issue (3): 275-281.DOI: 10.1007/s13659-017-0131-0

Construction of Spirooxindole Skeleton Through Intramolecular Dieckmann Cyclization

Ting Wu¹, Zhiqiang Pan², Chengfeng Xia²

1. The Key Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of Sciences, Guiyang 55002, China;
2. Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China

Received:2017-03-23 Revised:2017-04-30 Online:2018-02-06 Published:2017-06-24
Supported by:
This work was financially supported by the Natural Science Foundation of Yunnan Province (2014FA008 and 2015FB167),and the Program for Changjiang Scholars and Innovative Research Team in University (IRT13095).

Construction of Spirooxindole Skeleton Through Intramolecular Dieckmann Cyclization

Ting Wu¹, Zhiqiang Pan², Chengfeng Xia²

1. The Key Laboratory of Chemistry for Natural Products of Guizhou Province, Chinese Academy of Sciences, Guiyang 55002, China;
2. Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, China

通讯作者: Chengfeng Xia,e-mail:xiacf@ynu.edu.cn
基金资助:
This work was financially supported by the Natural Science Foundation of Yunnan Province (2014FA008 and 2015FB167),and the Program for Changjiang Scholars and Innovative Research Team in University (IRT13095).

Abstract

Abstract: A highly efficient and direct approach was developed to construct the structurally diverse spirooxindole skeleton, which is an important basic motif in natural products. Both the 3,3'-pyrrolidonyl spirooxindoles and spiroindolin-2-one δ-lactones were smoothly obtained by the intramolecular Dieckmann cyclization of oxindoles in excellent yield under mild conditions.

Key words: Dieckmann reaction, Cyclization, Spirooxindole, Indole

摘要： A highly efficient and direct approach was developed to construct the structurally diverse spirooxindole skeleton, which is an important basic motif in natural products. Both the 3,3'-pyrrolidonyl spirooxindoles and spiroindolin-2-one δ-lactones were smoothly obtained by the intramolecular Dieckmann cyclization of oxindoles in excellent yield under mild conditions.

关键词: Dieckmann reaction, Cyclization, Spirooxindole, Indole

Ting Wu, Zhiqiang Pan, Chengfeng Xia. Construction of Spirooxindole Skeleton Through Intramolecular Dieckmann Cyclization[J]. Natural Products and Bioprospecting, 2017, 7(3): 275-281.

Ting Wu, Zhiqiang Pan, Chengfeng Xia. Construction of Spirooxindole Skeleton Through Intramolecular Dieckmann Cyclization[J]. 应用天然产物, 2017, 7(3): 275-281.

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Construction of Spirooxindole Skeleton Through Intramolecular Dieckmann Cyclization

Construction of Spirooxindole Skeleton Through Intramolecular Dieckmann Cyclization

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