The enantioselective synthesis of tetracyclic methyllycaconitine analogues

Sparrow, Kevin; Barker, David; Brimble, Margaret A.

doi:10.1016/j.tet.2011.08.026

Cited by 26 publications

(12 citation statements)

References 28 publications

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“…Brimble and co-workers reported the enantioselective synthesis of the ABEF ring systems of methyllycaconitine analogues (Scheme 27). 98 The elegant approached utilized sequential Diels-Alder reaction, aldol, Mannich, and Wacker-type cyclizations to furnish the tetracyclic scaffold 337. The enantioselective synthesis commenced with a cobalt(III)-salen complex 331 catalyzed Diels-Alder reaction between enal 329 and diene 330 to give the endoadduct 332 in excellent yield and enantioselectivity; the benzyl group on the amine was necessary to affect high enantioselectivity.…”

Section: Diels-alder Reactionsmentioning

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: Diels-alder Reactionsmentioning

confidence: 99%

Recent Advances Towards Syntheses of Diterpenoid Alkaloids

Dank¹,

Sanichar²,

Choo³

et al. 2019

Synthesis

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“…13 Oxidation of the sulfide 9 to the corresponding sulfoxide 10 was performed using NaIO 4 in 95% yield. 14 Pyrolytic elimination of sulfoxide 10 under refluxing xylene condition afforded olefin 6 in 98% yield. 15 Here, pyrolytic elimination was found to be a clean and high yielding reaction, and it is a good alternative reaction sequence for the construction of a vinyl group over other reduction–elimination sequence in terms of overall yield and cost effectiveness of the process.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of (±)-Quinagolide: A Potent D₂ Receptor Agonist for the Treatment of Hyperprolactinemia

Kadam

Kawale

2019

ACS Omega

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A potent dopamine (D 2 ) receptor agonist (±)-quinagolide, which is used for the treatment of hyperprolactinemia, was synthesized using the ring closing metathesis (RCM) approach from meta -hydroxybenzaldehyde as the starting material. The key features of this synthesis are pyrolytic elimination, late-stage expedient synthesis of functionalized trans-fused tetrahydropyridine-3-carboxylates from olefin 6 , via conjugate addition–elimination upon acetate 11 , followed by RCM and phenyliodine bis(trifluoroacetate) (PIFA)-mediated Hofmann rearrangement of piperidine-3-carboxamide, which enables the synthesis of 3-aminopiperidine skeleton of quinagolide. For the total synthesis of natural products such as ergot alkaloids, late-stage synthesis of functionalized trans-fused tetrahydropyridine-3-carboxylates using RCM and PIFA-mediated Hofmann rearrangement of piperidine-3-carboxamide, which allows quick access to the synthetically challenging 3-aminopiperidine skeleton, are the main achievements of the present work.

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“…At the final stage, the construction of the pyridone ring was accomplished by the aza-Wittig reaction. Thus, Jones oxidation of diol 19 followed by the in situ formation of acyl azide 21, 11…”

Section: Resultsmentioning

confidence: 99%