Rhodium‐Catalyzed Denitrogenative [3+2] Cycloaddition: Access to Functionalized Hydroindolones and the Framework of Montanine‐Type <i>Amaryllidaceae</i> Alkaloids

Yang, Hongjian; Hou, Shuping; Cheng, Tao; Zhao, Lu; Wang, Chao; Cheng, Bin; Li, Yun; Zhai, Hongbin

doi:10.1002/chem.201702893

Cited by 17 publications

(13 citation statements)

References 129 publications

(43 reference statements)

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“…Li and Zhai reported a Rh-catalyzed [3 + 2] cycloaddition of imino carbenes derived from N -sulfonyl-1,2,3-triazoles 50.1 with cyclic silyl dienol ethers 50.2 to form various functionalized hydroindolones 50.4 (Scheme ). The synthetic applicability of the present protocol was demonstrated by the synthesis of the 5,11-methanomorphanthridine framework, which is extensively found in montanine-type Amaryllidaceae alkaloids. Additionally, synthetically valuable bicyclo[3.3.1]alkenone derivatives and pyrrolidine-ring-containing bicyclic indole compounds have been synthesized by utilizing this strategy.…”

Section: Denitrogenative Transformations Of Triazolesmentioning

confidence: 97%

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

2022

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Readily accessible and shelf-stable 1,2,3-triazole and its analogues such as pyridotriazole, triazoloindole, benzotriazole, and thiadiazole exist in equilibrium with their ring-opened isomers, viz., diazo compounds. These ring-opened isomers could be trapped by various metal catalysts (e.g., Rh, Pd, Cu, Co, Ag, etc.) to generate the corresponding metal carbenoids with extrusion of nitrogen. As a consequence, these unique N-heterocycles facilitate access to a realm of N-containing complex structural motifs of biological importance through denitrogenative transformations such as transannulations, insertions, ylide formation, and rearrangements by trapping of the metal carbenoids with a diverse range of coupling partners (e.g., alkenes, alkynes, nitriles, carbo/heterocycles, X–H/C–X bonds, etc.). Hence, suitably substituted triazole derivatives have emerged as efficient surrogates of diazo compounds for the generation of reactive metal carbenoids during the past decades. In this comprehensive review, we aim to discuss in detail the remarkable advancement in their synthesis and synthetic applications.

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Section: Denitrogenative Transformations Of Triazolesmentioning

confidence: 97%

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

2022

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“…The unique structural features and promising biological activities associated with montanine-type AA and their low content in plant material have attracted considerable synthetic efforts [29,30,39,40,49,[74][75][76][77][78][79][80][81][82][83][84][85][86][87][88][89][90][91]. However, most synthetic approaches involve many steps and low yield.…”

Section: Preparation Of Montanine-type Alkaloids By Rearrangement Of Haemanthamine-type Ring Systemmentioning

confidence: 99%

Chemical and Biological Aspects of Montanine-Type Alkaloids Isolated from Plants of the Amaryllidaceae Family

et al. 2020

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Plants of the Amaryllidaceae family are promising therapeutic tools for human diseases and have been used as alternative medicines. The specific secondary metabolites of this plant family, called Amaryllidaceae alkaloids (AA), have attracted considerable attention due to their interesting pharmacological activities. One of them, galantamine, is already used in the therapy of Alzheimer’s disease as a long acting, selective, reversible inhibitor of acetylcholinesterase. One group of AA is the montanine-type, such as montanine, pancracine and others, which share a 5,11-methanomorphanthridine core. So far, only 14 montanine-type alkaloids have been isolated. Compared with other structural-types of AA, montanine-type alkaloids are predominantly present in plants in low concentrations, but some of them display promising biological properties, especially in vitro cytotoxic activity against different cancerous cell lines. The present review aims to summarize comprehensively the research that has been published on the Amaryllidaceae alkaloids of montanine-type.

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“…In 2017, Li, Zhai and co‐workers described a Rh‐catalyzed denitrogenative [3+2] cycloaddition of N ‐sulfonyl‐1,2,3‐triazoles with cyclic silyl dienol ethers to synthesize functionalized hydroindolones (Scheme ). As suggested, upon treatment with rhodium catalysts, the N ‐sulfonyl‐1,2,3‐triazoles 136 was converted to α‐iminocarbene intermediate 138 .…”

Section: Synthetic Utilities Of Rhodium‐iminocarbenementioning

confidence: 99%

The Expanding Utility of Rhodium‐Iminocarbenes: Recent Advances in the Synthesis of Natural Products and Related Scaffolds

Yang

Zhai

2018

Chemistry A European J

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Rhodium-iminocarbenes that are derived from N-sulfonyl-1,2,3-triazoles have become an important class of reactive species and useful intermediates in organic synthesis. Over the last several years, many practical and versatile approaches involving rhodium-iminocarbene intermediates to synthetically challenging molecules (scaffolds) have been developed. This Minireview mainly summarizes the recent advance of rhodium-iminocarbene involved reactions in the synthesis of natural products and their related scaffolds by the end of 2017. Several applications in important pharmaceuticals are documented as well.

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Rhodium‐Catalyzed Denitrogenative [3+2] Cycloaddition: Access to Functionalized Hydroindolones and the Framework of Montanine‐Type Amaryllidaceae Alkaloids

Cited by 17 publications

References 129 publications

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

1,2,3-Triazole and Its Analogues: New Surrogates for Diazo Compounds

Chemical and Biological Aspects of Montanine-Type Alkaloids Isolated from Plants of the Amaryllidaceae Family

The Expanding Utility of Rhodium‐Iminocarbenes: Recent Advances in the Synthesis of Natural Products and Related Scaffolds

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