Total synthesis of rupestine G and its epimers

Yusuf, Abdullah; Zhao, Jiaheng; Wang, Bianlin; Aibibula, Paruke; Aisa, Haji Akber; Huang, Guozheng

doi:10.1098/rsos.172037

Cited by 9 publications

(6 citation statements)

References 32 publications

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“…It must be noted that rupestine E ( 5a ; 5R , 8S ‐isomer) was incorrectly assigned and reported as rupestine ( 5R , 8R ‐ isomer; 5b ; Figure ). Rupestine ( 5b ; 5R , 8R ‐ isomer) has never been isolated as a natural compound, and thus, rupestine ( 5b ; 5R , 8R ‐ isomer) cited in the earlier literature should be considered as rupestine E ( 5a ; 5R , 8S ‐ isomer; He et al, ; Su et al, ; Su, Wu, He, Slukhan, & Aisa, ; Yusuf et al, ). In his second attempt, Su et al () isolated four new guaipyridine sesquiterpene alkaloids, named as rupestine A, B, C, and D ( 1 – 4 , respectively; 4 as a nor‐rupestine; Figure ) from the flowers of A .…”

Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

“…rupestris L and reported eight guaipyridine sesquiterpene alkaloids named rupestine F–M ( 6 – 13 ; Figure ). Naturally, rupestine B and C ( 1 and 2 ) and rupestine H and I ( 8 and 9 ), as well as rupestine L and M (12 and 13) , exist as natural isomeric compounds (Yusuf et al, ).…”

Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

“…(Shelton, ). Although similar type of alkaloids have been synthesized by various groups (Craig & Henry, ; Yusuf et al, ), however, the rare existence and enhancement of the potential of rupestine ( 1 – 13 ) and (−)‐cananodine have provoked the necessity of isolating its other rupestine analogs from natural sources.…”

Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

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The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

Rashid

Alamzeb²,

Ali³

et al. 2019

Phytotherapy Research

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Several reviews have been published on Artemisia's derived natural products, but it is the first attempt to review the chemistry and pharmacology of more than 80 alkaloids and allied nitrogen compounds obtained from various Artemisia species (covering the literature up to June 2018). The pharmacological potential and unique skeleton types of certain Artemisia's alkaloids provoke the importance of analyzing Artemisia species for bioactive alkaloids and allied nitrogen compounds. Among the various types of bioactive Artemisia's alkaloids, the main classes were the derivatives of rupestine (pyridine–sesquiterpene), lycoctonine (diterpene), pyrrolizidine, purines, polyamine, peptides, indole, piperidine, pyrrolidine, alkamides, and flavoalkaloids. The rupestine derivatives are Artemisia's characteristic alkaloids, whereas the rest are common alkaloids found in the family Asteraceae and chemotaxonomically links the genus Artemisia with the tribes Anthemideae. The most important biological activities of Artemisia's alkaloids are including hepatoprotective, local anesthetic, β‐galactosidase, and antiparasitic activities; treatment of angina pectoris, opening blocked arteries, as a sleep‐inducing agents and inhibition of HIV viral protease, CYP450, melanin biosynthesis, human carbonic anhydrase, [3H]‐AEA metabolism, kinases, and DNA polymerase β1. Some of the important nitrogen metabolites of Artemisia include pellitorine, zeatin, tryptophan, rupestine, and aconitine analogs, which need to be optimized and commercialized further.

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Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

Section: The Chemistry and Pharmacology Of Artemisia Alkaloids/alliedmentioning

confidence: 99%

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The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

Rashid

Alamzeb²,

Ali³

et al. 2019

Phytotherapy Research

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“…Huang and co‐workers presented the first total synthesis of rupestine G 282 (Scheme 30), [211] a guaipyridine sesquiterpene alkaloid with 7‐membered carbocycle fused to pyridine ring, extracted from Artemisia rupestris L. In this reaction sequence, the RCM was utilized in late‐stage steps to furnace the compound 281 . The Suzuki coupling reaction between an aryl bromide 279 and isopropenyl boronic acid pinacol ester catalysed by Pd(PPh 3 ) 4 directed the formation of a diene 280 , which was then subjected to the RCM in presence G‐II catalyst 2 to produce a bicyclic compound 281 (53%) with 7‐member ring system.…”

Section: Ring‐closing Metathesis (Rcm)mentioning

confidence: 99%

Metathesis Reactions in Natural Product Fragments and Total Syntheses

et al. 2022

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The passion of total‐ and fragments syntheses of natural products always remained one of the top priorities among the synthetic chemists worldwide. Due their curiosity toward the complexity of molecules of living nature and their endeavour to imitate them in laboratory; limitless arrays of natural products have been extracted, architecturally‐elucidated, synthesized, and chronicled by utilizing various synthetic methodologies in different fashions. Frequently, the synthesis of complex natural products proceed with inscrutable synthetic challenges, which can be circumvented either by modification of previously developed synthetic methods or by formulating a new one. In this way, a myriad of powerful synthetic reactions have been developed since the genesis of the logic of chemical synthesis. Amongst them, metathesis tactics discovered unexpectedly in the 1950s (Nobel Prize in 2005), have incredibly influenced and changed the landscape of the art of the total and formal synthesis in the last three A. H. Hoveyda, A. R. Zhugralin, me abruptly as compared to other developed transformations or their modified forms. In this particular review article, we envisioned to report a comprehensive detail of the metathetic tools involved in both total and fragments synthesis of natural products in the years 2018 and 2019 along with an overview of 2017.

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“…Cananodine ( 6 ) has the most recognized biological activity in the family and shows potent and selective anticancer activity against hepatocytes (IC 50 0.94 μM, Hep G2 cells). 5 In part due to this bioactivity, 6 and other guaipyridines have attracted both synthetic attention 6 7 8 9 10 11 12 and renewed isolation efforts. 2 3 13 14…”

mentioning

confidence: 99%

Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone

Scheerer¹,

Leeth²,

Sprow³

2023

Synthesis

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A new method to prepare 1,4-oxazinone intermediates was developed based on aza-conjugate addition of β-amino alcohols to electron-deficient alkyne precursors. A tandem intramolecular cycloaddition/cycloreversion reaction sequence was evaluated, leading to the synthesis of the guaipyridine alkaloid natural products rupestine M and L. Starting from (–)-citronellal and thus a known configuration of the C5 stereocenter, a revised absolute configuration of natural rupestine L is suggested based on optical rotation.

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Total synthesis of rupestine G and its epimers

Cited by 9 publications

References 32 publications

The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

The chemistry and pharmacology of alkaloids and allied nitrogen compounds fromArtemisiaspecies: A review

Metathesis Reactions in Natural Product Fragments and Total Syntheses

Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone

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