First asymmetric enantioselective total synthesis of phenanthridine alkaloid, (S)-(+)-asiaticumine and its enantiomer

Nishiyama, Takashi; Takaiwa, Shuuya; Kotouge, Rika; Tani, Satomi; Yoshinaga, Rikako; Hamada, Erina; Endo, Mai; Sugino, Yuka; Hatae, Noriyuki; Hibino, Satoshi; Choshi, Tominari

doi:10.1016/j.tetlet.2019.151278

Cited by 5 publications

(2 citation statements)

References 45 publications

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“…These findings represent a significant advancement in the field of asymmetric synthesis and pave the way for further exploration of the biological activities of this natural product. 77 Further, the Suzuki cross-coupling reaction is a widely used method for the synthesis of carbon–carbon bonds. Dende et al demonstrated the successful application of Suzuki cross-coupling reaction in the synthesis of phenanthridine derivatives 162 (Scheme 37 ) using suitably substituted aromatic o -bromo N -tosylhydrazones 160 and 2′-aminobenzeneboronic acid 161 under microwave irradiation.…”

Section: Phenanthridine Hybridsmentioning

confidence: 99%

Microwave-Assisted Synthesis of Heterocyclic Scaffolds

Agarwal,

Kumar,

Maurya

2024

SynOpen

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In recent years, there has been a notable surge in the utilization of microwave energy, leading to the emergence of innovative and groundbreaking methods across various branches of chemistry, including organic synthesis, materials science, heterocyclic chemistry, and medicinal chemistry. This comprehensive literature review delves into the microwave-assisted organic synthesis of specific heterocycles, illuminating its effectiveness in producing diverse molecules with heightened efficiency and selectivity. The review highlights the significant role of microwave irradiation as a potent method for constructing a wide range of compounds. Particular emphasis is placed on the impact of the technique on synthesizing various hybrids such as 1,2,3-triazole hybrids, coumarin hybrids, imidazopyridine hybrids, phenanthridines hybrids, carbene hybrids, and oxazole hybrids. This article is valuable as it offers insights into current synthetic procedures and trends in developing innovative medications utilizing heterocyclic compounds.1 Introduction2 Synthesis of 1,2,3-Triazole Hybrids3 Coumarin Hybrids4 Imidazo Pyridine Hybrids5 Phenanthridine Hybrids6 Carbene Hybrids7 Oxazole Hybrids8 Conclusion

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Section: Phenanthridine Hybridsmentioning

confidence: 99%

Microwave-Assisted Synthesis of Heterocyclic Scaffolds

Agarwal,

Kumar,

Maurya

2024

SynOpen

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“…Our research group has been interested in the unique structure and pharmacological action of condensed heteroaromatic compounds and we have been searching for highly active compounds based on these naturally occurring compounds and their derivatives. To date, we have achieved the total synthesis of several such compounds using various types of 6π-electron system (hexatriene, 1- and 2-azahexatriene) electrocyclic reactions, such as asiaticumine [ 27 ], marinoquinolines [ 28 ], trigonoine B [ 29 ], girinimbine [ 30 ], and karnatakafuran B [ 31 ]. We have also published the total synthesis of ( R )-(–)-pyridindolols using another synthetic approach that involved thermal cyclization of 3-alkynylindole-2-aldoxime to construct the key β-carboline N -oxide intermediate [ 32 , 33 ].…”

Section: Introductionmentioning

confidence: 99%

Novel Approach to the Construction of Fused Indolizine Scaffolds: Synthesis of Rosettacin and the Aromathecin Family of Compounds

Mizuno,

Nishiyama,

Endo

et al. 2023

Molecules

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Camptothecin-like compounds are actively employed as anticancer drugs in clinical treatments. The aromathecin family of compounds, which contains the same indazolidine core structure as the camptothecin family of compounds, is also expected to display promising anticancer activity. Therefore, the development of a suitable and scalable synthetic method of aromathecin synthesis is of great research interest. In this study, we report the development of a new synthetic approach for constructing the pentacyclic scaffold of the aromathecin family by forming the indolizidine moiety after synthesizing the isoquinolone moiety. Thermal cyclization of 2-alkynylbenzaldehyde oxime to the isoquinoline N-oxide, followed by a Reissert–Henze-type reaction, forms the key strategy in this isoquinolone synthesis. Under the optimum reaction conditions for the Reissert–Henze-type reaction step, microwave irradiation-assisted heating of the purified N-oxide in acetic anhydride at 50 °C reduced the formation of the 4-acetoxyisoquinoline byproduct to deliver the desired isoquinolone at a 73% yield after just 3.5 h. The eight-step sequence employed afforded rosettacin (simplest member of the aromathecin family) at a 23.8% overall yield. The synthesis of rosettacin analogs was achieved by applying the developed strategy and may be generally applicable to the production of other fused indolizidine compounds.

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Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

et al. 2021

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Phenanthridine derivatives are one of the most intensively studied families of biologically active compounds. There has been considerable scientific interest in the turn of this century in the synthesis of these N‐containing heterocycles as they are prevalent in many alkaloids and also possess striking biological activities including antibacterial, antifungal, antitumor activities. In this regard, a number of synthetic approaches toward the construction of phenanthridine moieties with various substituents, and to increase their yield have been developed by the synthetic organic community. Even though many researchers have developed various innovative methods for the synthesis of phenanthridine derivatives for the past few years, still there is substantial scope for the discovery of novel synthetic methods. In this review, the latest developments in the diverse synthetic strategies of phenanthridine derivatives in the presence and absence of metals were described. The present review also enlightens the use of different reagents, the diversity of the substrates identified, and the plausible mechanisms unravelled towards the construction of these biologically relevant scaffolds.

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First asymmetric enantioselective total synthesis of phenanthridine alkaloid, (S)-(+)-asiaticumine and its enantiomer

Cited by 5 publications

References 45 publications

Microwave-Assisted Synthesis of Heterocyclic Scaffolds

Microwave-Assisted Synthesis of Heterocyclic Scaffolds

Novel Approach to the Construction of Fused Indolizine Scaffolds: Synthesis of Rosettacin and the Aromathecin Family of Compounds

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

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