Silver catalyzed cascade synthesis of alkaloid ring systems: concise total synthesis of fascaplysin, homofascaplysin C and analogues

Waldmann, Herbert; Eberhardt, Luc; Wittstein, Kathrin; Kumar, Kamal

doi:10.1039/c001350a

Cited by 84 publications

(34 citation statements)

References 49 publications

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“…Similarly, a cascade reaction sequence involving silvercatalyzed cycloisomerization of acetylenic aldehydes as the key transformation was recently explored in the synthesis of diverse alkaloid ring systems. [55] Indoloisoquinolines, a medicinally significant class of molecules known for their anticancer properties, were readily and efficiently generated by using this cascade approach. Thus, the imine generated from an acetylenic benzaldehyde 55 and an aniline with a pendant nucleophile 56 underwent the key silvercatalyzed cycloisomerization reaction under microwave conditions to yield the isoquinolinium cations 58.…”

Section: Bios In the Development Of Compound Collectionsmentioning

confidence: 99%

Biology‐Oriented Synthesis

et al. 2011

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Which compound classes are best suited as probes and tools for chemical biology research and as inspiration for medicinal chemistry programs? Chemical space is enormously large and cannot be exploited conclusively by means of synthesis efforts. Methods are required that allow one to identify and map the biologically relevant subspaces of vast chemical space, and serve as hypothesis-generating tools for inspiring synthesis programs. Biology-oriented synthesis builds on structural conservatism in the evolution of proteins and natural products. It employs a hierarchical classification of bioactive compounds according to structural relationships and type of bioactivity, and selects the scaffolds of bioactive molecule classes as starting points for the synthesis of compound collections with focused diversity. Navigation in chemical space is facilitated by Scaffold Hunter, an intuitively accessible and highly interactive software. Small molecules synthesized according to BIOS are enriched in bioactivity. They facilitate the analysis of complex biological phenomena by means of acute perturbation and may serve as novel starting points to inspire drug discovery programs.

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Section: Bios In the Development Of Compound Collectionsmentioning

confidence: 99%

Biology‐Oriented Synthesis

et al. 2011

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“…Recently some reports have shown that silver salt catalysts or co-catalysts efficiently promoted organic reactions [13,14]. Significant development of palladium(0)/silver salt catalyzed cross-coupling reactions has occurred only in the past decade.…”

Section: Introductionmentioning

confidence: 99%

Pd(PPh3)4/AgOAc-catalyzed one-pot synthesis of substituted 3,4-dihydronaphthalen-1(2H)-ones

Liu

Yan

et al. 2011

Monatsh Chem

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A novel and efficient one-pot synthesis of 3,4-dihydronaphthalen-1(2H)-ones by employing 2-iodocyclohex-2-enones, 1-alkynes, and a Pd[(C 6 H 5 ) 3 P] 4 /AgOAc catalytic system is described. The attractive features of this method, which enables the facile preparation of 3,4-dihydronaphthalen-1(2H)-one derivatives, are its very simple and straightforward procedure, mild reaction conditions, and good yields (65-87%).

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“…The intermediates also lead to interesting carbazoles,14 dihydroisoquinolines15 and isoquinolines 16. Furthermore, they have been applied in the total synthesis of azaphilones,4c,17 fascaplysin,18 heliophenanthrone,5a and (+)‐ochromycinone 19…”

Section: Introductionmentioning

confidence: 99%

Iodine/Water‐Mediated Oxidation of o‐Alkynylaroyl Compounds and Application of the Products of Oxidation in the Synthesis of Nitrogen Heterocycles

Sakthivel¹,

Srinivasan²

2013

Eur J Org Chem

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A facile iodine/water‐mediated oxidation of the triple bond of o‐alkynylaroyl compounds to furnish tricarbonyl compounds is reported. The reaction proceeds through the formation of isochromenol intermediates by the assistance of the neighbouring aroyl group. The product tricarbonyl compounds are versatile synthetic precursors that, upon treatment with mono‐ and diamines, hydrazines and amino alcohols, afford various heterocyclic scaffolds such as isoindolinones, phthalazines, benzimidazoisoquinolinones, quinoxalines and benzimidazole‐quinoxaline hybrid compounds. Mechanistic aspects of the formation of the above heterocycles are discussed. Finally, a short synthetic route to the isoindolinone natural product, aristolactam BII is reported.

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Silver catalyzed cascade synthesis of alkaloid ring systems: concise total synthesis of fascaplysin, homofascaplysin C and analogues

Abstract: A silver catalyzed and microwave assisted one-pot cascade synthesis provides efficient access to diverse alkaloid-inspired scaffold classes, and a concise and efficient total synthesis of homofascaplysin C and fascaplysin.

Cited by 84 publications

References 49 publications

Biology‐Oriented Synthesis

Biology‐Oriented Synthesis

Pd(PPh3)4/AgOAc-catalyzed one-pot synthesis of substituted 3,4-dihydronaphthalen-1(2H)-ones

Iodine/Water‐Mediated Oxidation of o‐Alkynylaroyl Compounds and Application of the Products of Oxidation in the Synthesis of Nitrogen Heterocycles

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