Rapid construction of the unique BCD ring system of tricyclo[6.2.1.0]undecane in the C 19 -diterpenoid alkaloid aconitine

Yang, Xue; Cheng, Bin; Cheng, Hang; Xu, Liang; Wang, Jianli

doi:10.1016/j.cclet.2017.03.032

Cited by 10 publications

(2 citation statements)

References 31 publications

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“…A similar PIDA-promoted oxidative cyclization strategy was applied by Xu, Wang, and co-workers to furnish the BCD ring systems of aconitine (27) (Scheme 32). 103 Treatment of phenol 374 with PIDA in the presence of methanol resulted in the dimer 375. Fortunately, the desired cycloadduct 376 was formed under thermodynamic conditions to induce a retro-[4+2]/intramolecular Diels-Alder reaction from 375; reduction of the ketone in 376 provided alcohol 377.…”

Section: Oxidative Dearomatization/diels-alder Sequencementioning

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: Oxidative Dearomatization/diels-alder Sequencementioning

confidence: 99%

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Dank¹,

Sanichar²,

Choo³

et al. 2019

Synthesis

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“…Liu and Qin [ 86 ] highlighted the importance of dearomatization of aromatic compounds that yield o -benzoquinones coupled with Diels–Alder cycloaddition in the synthesis of complex structures such as 83 , 84 , 85 , and many others. Yang et al constructed a unique tricyclo [6.2.1.0] BCD-system 86 of the NDA skeleton ( Figure 12 ) [ 87 ].…”

Section: Norditerpenoid Alkaloid (Nda) Biodiversitymentioning

confidence: 99%

Poisonous Piperidine Plants and the Biodiversity of Norditerpenoid Alkaloids for Leads in Drug Discovery: Experimental Aspects

Qasem

Rowan

Blagbrough

2022

IJMS

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There are famous examples of simple (e.g., hemlock, Conium maculatum L.) and complex (e.g., opium poppy, Papaver somniferum L., Papaveraceae) piperidine-alkaloid-containing plants. Many of these are highly poisonous, whilst pepper is well-known gastronomically, and several substituted piperidine alkaloids are therapeutically beneficial as a function of dose and mode of action. This review covers the taxonomy of the genera Aconitum, Delphinium, and the controversial Consolida. As part of studying the biodiversity of norditerpenoid alkaloids (NDAS), the majority of which possess an N-ethyl group, we also quantified the fragment occurrence count in the SciFinder database for NDA skeletons. The wide range of NDA biodiversity is also captured in a review of over 100 recently reported isolated alkaloids. Ring A substitution at position 1 is important to determine the NDA skeleton conformation. In this overview of naturally occurring highly oxygenated NDAs from traditional Aconitum and Delphinium plants, consideration is given to functional effect and to real functional evidence. Their high potential biological activity makes them useful candidate molecules for further investigation as lead compounds in the development of selective drugs.

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Recent advances in total synthesis of natural products by masked ortho‐benzoquinones

Chen

Hsieh

2022

J Chinese Chemical Soc

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The Diels-Alder adducts of masked ortho-benzoquinone (MOB) normally perform high regio-and stereoselectivity and are generated under mild conditions.The advantages of MOB include: (a) Containing highly functional moieties: alkene, diene, carbonyl, enone, and dienone; (b) Easily accessible from 2-methoxyphenol derivatives via oxidative dearomatization, and related 2-methoxyphenol easily prepared from commercially available starting materials; (c) The Diels-Alder adducts possessing unique features such as regio-and stereoselectivity and at least four contiguous stereogenic centers in one step. Furthermore, related bicyclo[2.2.2]octenone skeleton can be applied to further complex structure construction by various chemical transformations, such as radical cyclization, oxa-di-π-methane rearrangement, Beckwith-Dowd rearrangement, hydrogen atom transfer reaction, Cope rearrangement, Wanger-Meerwein rearrangement, carbonyl-ene reaction, aldol reaction, ring opening etc. Among these advantages, MOB system is prospected to continue as an important intermediate for total synthesis of natural products.

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Rapid construction of the unique BCD ring system of tricyclo[6.2.1.0]undecane in the C 19 -diterpenoid alkaloid aconitine

Cited by 10 publications

References 31 publications

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Poisonous Piperidine Plants and the Biodiversity of Norditerpenoid Alkaloids for Leads in Drug Discovery: Experimental Aspects

Recent advances in total synthesis of natural products by masked ortho‐benzoquinones

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