Synthese des Narciprimins und verwandter Verbindungen

Mondon, Albert; Krohn, Karsten

doi:10.1002/cber.19721051127

Cited by 22 publications

(5 citation statements)

References 23 publications

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“…Recrystallization of the Rf 0.46 anticancer component (T/C 138'->165 at 0.751->6.0 mg/kg dose levels and 206 at 12.5 mg/kg in the PS system with ED50, 0.01 µg/mI) from DMF/MeOH/Et20 gave a pure specimen that displayed elemental analyt-5In July 1972 (10), the lycoricidine name was suggested as a replacement for margetine. Since the term narciclasine (2c) is now well established, we suggest that margetine/lycoricidine be replaced by the simplification 7-deoxynarciclasine (2a).…”

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confidence: 99%

Antineoplastic Agents, 120. Pancratium littorale

et al. 1986

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The bulbs of Pancratium littorale collected in Hawaii were found to contain a new phenanthridone biosynthetic product designated pancratistatin (4a) that proved to be effective (38-106% life extension at 0.75-12.5 mg/kg dose levels) against the murine P-388 lymphocytic leukemia. Pancratistatin also markedly inhibited (ED50, 0.01 microgram/ml) growth of the P-388 in vitro cell line and in vivo murine M-5076 ovary sarcoma (53-84% life extension at 0.38-3.0 mg/kg). An X-ray crystal structure determination of pancratistatin monomethyl ether (4c) and a detailed high resolution (400 MHz) nmr study of pancratistatin and its pentaacetate (4b) completed assignment of structure 4a. Companion antineoplastic constituents of P. littorale were found to be narciclasine (2c) and its 7-deoxy derivative (2a). The structure of 7-deoxynarciclasine (2c) was also confirmed by an X-ray crystallographic analysis.

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confidence: 99%

Antineoplastic Agents, 120. Pancratium littorale

et al. 1986

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“…Recently, photocatalyzed reactions proved to be a valuable method for the synthesis of heterocycles and biologically active compounds [ 137 ]. Firstly, Mondon et al investigated the photocyclization of benzanilides to furnish unsymmetrically substituted phenanthridinones [ 138 ]. Later, Prabhakar et al reported an improved phenanthridinone synthesis by using the photocylization of boron complexes, followed by hydrolysis [ 139 ].…”

Section: Photo-mediated Reactions For Phenanthridinone Synthesismentioning

confidence: 99%

Synthetic Strategies in the Preparation of Phenanthridinones

et al. 2021

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Phenanthridinones are important heterocyclic frameworks present in a variety of complex natural products, pharmaceuticals and displaying wide range of pharmacological actions. Its structural importance has evoked a great deal of interest in the domains of organic synthesis and medicinal chemistry to develop new synthetic methodologies, as well as novel compounds of pharmaceutical interest. This review focuses on the synthesis of phenanthridinone scaffolds by employing aryl-aryl, N-aryl, and biaryl coupling reactions, decarboxylative amidations, and photocatalyzed reactions.

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“…The photoinduced B-ring cyclization has been investigated in the context of the title alkaloids synthesis [130]. The photocyclization of enamide [131] was used by Rigby and coworkers in the first total synthesis of (+)-narciclasine [132] and in the synthesis of (+)-pancratistatin [133].…”

Section: Iii-2-2) Intramolecular Coupling Of the A-ring And Preformedmentioning

confidence: 99%

Chemistry and Synthesis of Highly Oxygenated Alkaloids from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin and Analogs

Chapleur¹,

Chrétien²,

Ahmed³

et al. 2006

COS

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Plants of the genus Amaryllidaceae produce a number of alkaloids and other non-basic related molecules, some of them showing antitumor activities. The low availability of these often-complex structures, coupled with their interesting biological properties, has stimulated a long-standing interest in the chemistry community. Total syntheses of challenging structures such as lycoricidine, narciclasine and pancratistatin, which are highly oxygenated tetracyclic systems comprising up to six contiguous chiral centers on ring C, have been accomplished. These well-known structures, more than thirty years for lycoricidine, continue to stimulate interest in synthetic work to provide enough synthetic material or analogs, and also are a model target to test or develop new synthetic methodologies. The synthetic studies around these complex phenanthridinones made use of the latest up-to-date synthetic methodologies and led to the development of novel methods of functionalization and carbon-carbon bond formation. The purpose of this review is to summarize recent total syntheses and synthetic approaches towards these three highly oxygenated members of this particular class of alkaloids over the last twenty years. The review is arranged according to the different strategies used for the construction of the benzophenanthridinone ring system.

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Synthese des Narciprimins und verwandter Verbindungen

Cited by 22 publications

References 23 publications

Antineoplastic Agents, 120. Pancratium littorale

Antineoplastic Agents, 120. Pancratium littorale

Synthetic Strategies in the Preparation of Phenanthridinones

Chemistry and Synthesis of Highly Oxygenated Alkaloids from Amaryllidaceae: Lycoricidine, Narciclasine, Pancratistatin and Analogs

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