Reductive cyclization strategy for construction of the highly oxygenated CD ring system of aconitine

Matsuzawa, Akinobu; Kasamatsu, Akihiko; Sugita, Kazuyuki

doi:10.1016/j.tetlet.2016.08.096

Cited by 7 publications

(2 citation statements)

References 29 publications

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“…96 Sugita and co-workers reported a reductive cyclization strategy of ,-epoxy ketone 322 to synthesize the CD ring system of aconitine (27) (Scheme 26). 97 SmI 2 initiates the formation of samarium enolate 323 that subsequently underwent an intramolecular aldol cyclization with the pendant aldehyde. The reaction was expected to proceed through cyclic transition state 324.…”

Section: Reductive Couplingmentioning

confidence: 99%

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Dank¹,

Sanichar²,

Choo³

et al. 2019

Synthesis

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The diterpenoid alkaloids serve as a rich source of synthetic targets for organic chemists, due to the intriguing structure of the overlapping ring systems, along with biological activities commonly associated with compounds of this group. Fifteen total syntheses and numerous synthetic studies towards construction of ring fragments have been reported since 2010. This review article gives a brief overview of diterpenoid alkaloids and summarizes the recent synthetic efforts.1 Introduction1.1 Structural Classification and Biosynthetic Origin1.2 Structure Elucidation of the Aconitum Alkaloids2 Total Syntheses2.1 C18-Diterpenoid Alkaloids2.2 C19-Diterpenoid Alkaloids2.3 C20-Diterpenoid Alkaloids3 Strategies To Synthesize Ring Systems3.1 Radical-Based Cyclizations3.2 Ruthenium-Mediated Enyne Cycloisomerization3.3 Reductive Coupling3.4 Diels–Alder Reactions3.5 Oxidative Dearomatization/Diels–Alder Sequence3.6 Transannular Aziridation3.7 Intramolecular [5+2] Cycloaddition3.8 Miscellaneous4 Conclusion

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Section: Reductive Couplingmentioning

confidence: 99%

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Dank¹,

Sanichar²,

Choo³

et al. 2019

Synthesis

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show abstract

“…Natural botanical insecticides have attracted wide attention because of their high efficiency, less residues, and compliance with environmental factors. Since the 1960s, many scholars have conducted in-depth studies on the separation [20,21], determination [22], and application of aconitine [23][24][25]. Pu et al [26] reported an unexpected crystal structure of aconitine and revealed the main reason for the spontaneous transformation of aconitine solid powders into crystals in air.…”

Section: The Crystal Structure Of Aconitinementioning

confidence: 99%

Research progress of plant-derived aconitine as insecticide

Yan¹,

Liu²,

Li³

2022

ScienceAsia

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In recent years, increasing attention is being given to the effective protection of the environment. The use of pesticides is a common practice in agriculture. At present, finding effective and safe pesticides is important for research in agricultural application. Botanical insecticides are environmentally friendly because of their environmental viability and easy degradation. However, there are still some problems in the development and utilization of botanical insecticides leading to a bottleneck in the process. In order to facilitate the development of botanical insecticides, this review uses aconitine as an example to summarize the research progress, the detection and analysis, and the carrier materials to optimize its usage and storage.

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The diterpenoid alkaloids

Liu

Qin

et al. 2022

The Alkaloids: Chemistry and Biology

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Reductive cyclization strategy for construction of the highly oxygenated CD ring system of aconitine

Cited by 7 publications

References 29 publications

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Research progress of plant-derived aconitine as insecticide

The diterpenoid alkaloids

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