Cascade Cyclization, Dipolar Cycloaddition to Bridged Tricyclic Amines Related to the <i>Daphniphyllum</i> Alkaloids

Coldham, Iain; Burrell, Adam J. M.; Guerrand, Hélène D. S.; Oram, Niall

doi:10.1021/ol102961x

Cited by 68 publications

(19 citation statements)

References 33 publications

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“…Coldham et al reported the first synthesis of the core ring system of the yuzurimine-type alkaloids by a cascade of condensation, cyclization, then intramolecular dipolar cycloaddition reactions [55]. In another study, a similar approach was successfully extended to bridged tricyclic compounds, yuzurimine B, daphnilactone B, and bukittinggine [56]. In 2009, two reports about asymmetric synthesis of cores common in daphnicyclidin-A-type alkaloids were published.…”

Section: Synthesis !mentioning

confidence: 99%

Daphniphyllum Alkaloids: Recent Findings on Chemistry and Pharmacology

Zhang

Ding

et al. 2013

Planta Med

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The unique polycyclic fused ring systems of Daphniphyllum alkaloids, along with their extensive bioactivities, make this family of alkaloids especially attractive targets for total synthesis and biogenetic studies. Successive discoveries of new alkaloids with unprecedented skeletons have made a great contribution to structural diversities of alkaloids elaborated by plants of the genus Daphniphyllum. By the end of 2008, more than 200 alkaloids belonging to 14 different skeletal types have been isolated from different parts of plants of thirteen Daphniphyllum species. These alkaloids show cytotoxic, antioxidant, vasorelaxant, and antiplatelet activating factor effects. The plausible biosynthetic pathways for Daphniphyllum alkaloids have been proposed and biomimetic total syntheses of some alkaloids completed. To provide an update of the previous reviews published in 2009, new structures, synthesis, and bioactivity of Daphniphyllum alkaloids reported in recent years are presented in this article. In the meantime, an additional 54 novel alkaloids have been isolated and identified. Among them, some possess unprecedented frameworks. Several inspired organic syntheses were completed.

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Section: Synthesis !mentioning

confidence: 99%

Daphniphyllum Alkaloids: Recent Findings on Chemistry and Pharmacology

Zhang

Ding

et al. 2013

Planta Med

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“…[9] Among the various available synthetic methodology, [3 + 2] cycloaddition play a key role for the construction of biologically significant five-membered heterocycles and azomethin ylide has been employed for the synthesis of pharmacologically important pyrrolidines, pyrrolizines and spiro compounds with high regio-and stereoselectivity. [10][11] Consequently, 1,2,3triazole derivatives show significant importance in the development of new perspective materials [12] and exhibit potential biological applications such as anti HIV-1, [13] antiparasitic, [14] antiplatelet, [15] antimicrobial against Gram positive bacteria, [16] selective b 3 adrenergic receptor agonism, [17] anticancer, [18] antimalarial [19] and anti-inflammatory activities. [20] 1,2,3-Triazole systems are remarkably stable towards hydrolytic, oxidative/ reductive conditions and enzymatic degradation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Electrochemical, Antibacterial and Anticancer Studies on Triazole‐Bridged Pyrrolidine‐Grafted Macrocycles via [3+2] Cycloaddition of Azomethin Ylide

2018

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An efficient and regioselective synthesis of triazole bridged pyrrolidine grafted macrocycle derivatives was accomplished by O‐alkylation, followed by aldol/Wittig reaction, click reaction with salicylaldehyde and finally by intramolecular 1, 3‐dipolar cycloaddition (1,3‐DC) to with azomethin ylide. The regio‐ and stereochemical outcome of the reaction was unambiguously established by single crystal X‐ray analysis of the cycloadducts. All the synthesized macrocycles exhibit irreversible oxidation reduction signals in cyclic voltammetry. Antioxidant property and antibacterial activity against Bacillus cereus and Klebsiella pneumoniae bacteria and anticancer activity against human adenocarcinoma breast cancer cell line cells (MCF‐7) revealed that all the pyrrolidine grafted macrocycles showed activity comparable to that of the standard drug.

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“…Moreover, our group has recently accomplished the asymmetric total syntheses of himalensine A 31 , dapholdhamine B 32 , and caldaphnidine O 33 . However, despite extensive synthetic studies [34][35][36][37][38][39][40][41][42][43][44][45][46][47][48] , total synthesis of yuzurimine-type alkaloids-the largest subfamily of the Daphniphyllum alkaloids-has not been achieved so far.…”

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confidence: 99%

Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J

Guo

Zhang

et al. 2020

Nat Commun

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Ever since Hirata's report of yuzurimine in 1966, nearly fifty yuzurimine-type alkaloids have been isolated, which formed the largest subfamily of the Daphniphyllum alkaloids. Despite extensive synthetic studies towards this synthetically challenging and biologically intriguing family, no total synthesis of any yuzurimine-type alkaloids has been achieved to date. Here, the first enantioselective total synthesis of (+)-caldaphnidine J, a highly complex yuzuriminetype Daphniphyllum alkaloid, is described. Key transformations of this approach include a highly regioselective Pd-catalyzed hydroformylation, a samarium(II)-mediated pinacol coupling, and a one-pot Swern oxidation/ketene dithioacetal Prins reaction. Our approach paves the way for the synthesis of other yuzurimine-type alkaloids and related natural products.

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Cascade Cyclization, Dipolar Cycloaddition to Bridged Tricyclic Amines Related to the Daphniphyllum Alkaloids

Cited by 68 publications

References 33 publications

Daphniphyllum Alkaloids: Recent Findings on Chemistry and Pharmacology

Daphniphyllum Alkaloids: Recent Findings on Chemistry and Pharmacology

Synthesis, Electrochemical, Antibacterial and Anticancer Studies on Triazole‐Bridged Pyrrolidine‐Grafted Macrocycles via [3+2] Cycloaddition of Azomethin Ylide

Asymmetric total synthesis of yuzurimine-type Daphniphyllum alkaloid (+)-caldaphnidine J

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