Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions

Varga, Szilárd; Angyal, Péter; Martin, Gábor; Egyed, Orsolya; Holczbauer, Tamás; Soós, Tibor

doi:10.1002/ange.202004769

Cited by 15 publications

(2 citation statements)

References 68 publications

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“…Minovincine (Varga et al 2020) [200] P 352.4 Rosicine (Atta et al 1984d) [26] L 324.3 Vincoline (Svoboda et al1964) [183] L, P 368.4 19-(S)-epimisiline (Peraza-Sanchez et al1998) [138] HR 368.4 Vindolinine (Kutney et al 1980) [97] ST, CS, L, P 368.4 Hörhammericine (Rijhwani and Shanks 1998) [157] ST, CS 368.4 Deacetoxyvindoline (Kutney et al 1980) [97] SD, L, P 398.5 11-methoxytabersonine (Sun et al2018) [118] F,P 366.4 16-Hydroxytabersonine (Sun et al2018) [118] CS, L, P 352.4 11-methoxyhörhammericine (Rijhwani and Shanks 1998) [157] ST,CS 398.4…”

Section: Mustafa Andmentioning

confidence: 99%

A review on phytochemical constituents and pharmacological properties of Catharanthus roseus (L.) G. Don

Sharma,

Singla,

Kaur

et al. 2024

J. Med. Plants Stud.

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Ethnopharmacological relevance: Catharanthus roseus (also called Sadabahar in India), is utilized as a common traditional medicine in India, England, Thailand, Japan and Australia. It was traditionally used to treat wasp string, gonorrhoea, hypertension and menstrual cycle. Various compounds obtained from this plant are utilizeds for medicinal purposes. It is even commercially formulated for its anticancer properties. Aims: This review aims to provide a systematic summary of Catharanthus roseus and to reveal the correlation between the traditional uses and pharmacological activities so as to offer inspiration for future research. Materials and methods: All corresponding information about Catharanthus roseus was collected using Google Scholar and from various scientific databases including Springer, Science Direct, Wiley, and PubMed. Local dissertations and books were searched as well. Results: According to classical ayurvedic text, Catharanthus roseus dominantly displays antidiabetic effect in diabetes mellitus person and its hypertension properties which were verified in modern medicine for their use. In modern research, more than 200 compounds were identified from Catharanthus roseus. Leaves contain large number of alkaloids along with flavonoids, sterols, saponins, amino acid, polyphenols and anthocyanins. Alkaloids such as vindoline, vincristine, vinblastine, and catharanthine, are considered as the characteristic and active constituents of this plant. They exhibited anticancer, antidiabetic, antivirus, antibacterial effects, etc. Vinblastine and vincristine acts on the cancer cells by disrupting the mitotic spindle fibres thereby inhibiting cell division. Currently, there is no lethal effect of Catharanthus roseus at lower dosage on human i.e., less than 5000 mg/kg. Conclusions: Due to pantropical distribution of C. roseus, it has wide range of traditional uses in different countries. Among these uses antitumor, anticancer and antidiabetic potentialswere further supported by scientific research and clinical trials to develop commercial medicine. For future research, still other traditional uses are yet to be authenticated so more in vivo experiments and clinical studies are encouraged to further clarify the relation between these traditional uses and their modern applications.

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Section: Mustafa Andmentioning

confidence: 99%

A review on phytochemical constituents and pharmacological properties of Catharanthus roseus (L.) G. Don

Sharma,

Singla,

Kaur

et al. 2024

J. Med. Plants Stud.

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“…Ma's group reported their synthesis of kopia alkaloids in 2018 through SmI 2 ‐mediated reductive coupling of keto and nitrile groups followed by an α‐ketol rearrangement, [17a] and in 2020, a Mannich type cyclization to establish the ring system of complex kopsinitarine E [17b] . Three other methods have been reported for the construction of the bicyclo [2.2.2] octane ring system along the way towards kopsia alkaloids in 2020, including a Fischer indole/Mannich cascade reaction by Soós's group, [18] an aldol cyclization by Tu's group, [19] and an intramolecular alkylation by Ye's group [20] . Most recently, in 2022, Jia's group reported an asymmetric Diels–Alder reaction to assemble the bicyclo [2.2.2] octane moiety [21]…”

Section: Introductionmentioning

confidence: 99%

Total Syntheses of Kopsaporine, Kopsinol and Kopsiloscine A

Zhang

Tian

et al. 2023

Angewandte Chemie

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Kopsia alkaloids represent a complex class of natural products bearing a polycyclic ring system with two or three consecutive quaternary carbon centers. In this article, we report the first total synthesis of Kopsaporine related alkaloids. Features of our structure‐unit‐based strategy are an intramolecular Pummerer rearrangement induced nucleophilic cyclization/aza‐Prins cyclization to construct the highly functional hexahydrocarbazole skeleton, an olefin migration vinylogous alkylation to establish the C20 all‐carbon quaternary center, an iridium complex mediated radical addition to fuse the aspidofractine framework, an unprecedented IBX oxidation to introduce the α‐hydroxyketone moiety, and a bioinspired retro‐Aldol/Aldol reaction to convert kopsaporine to kopsiloscine A.

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Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction

Wang

Zhuang

et al. 2020

Angewandte Chemie

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A tandem Bischler-Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine-type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids.

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Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions

Cited by 15 publications

References 68 publications

A review on phytochemical constituents and pharmacological properties of Catharanthus roseus (L.) G. Don

A review on phytochemical constituents and pharmacological properties of Catharanthus roseus (L.) G. Don

Total Syntheses of Kopsaporine, Kopsinol and Kopsiloscine A

Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction

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