Asymmetric Synthesis of (−)-1-Hydroxyquinolizidinone, a Common Intermediate for the Syntheses of (−)-Homopumiliotoxin 223G and (−)-Epiquinamide

Voituriez, Arnaud; Ferreira, Franck; Pérez-Luna, and Alejandro; Chemla, Fabrice

doi:10.1021/ol701952y

Cited by 47 publications

(18 citation statements)

References 20 publications

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“…In continuation of research work on the synthesis of 1,2amino alcohols, Chemla's group achieved the synthesis of (+)-β-conhydrine by carrying out the diastereoselective addition of lithium 3-(methoxymethoxy)allenylcuprates to enantiopure chiral N-tert-butylsulfinilimines in cis fashion (Scheme 31). 46,47 ral auxiliary (Scheme 32). 48 The hydrazone 108 on treatment with LDA followed by trapping with ethyl iodide gave 109 with 89% dr.…”

Section: Chiral Auxiliary Mediated Synthesismentioning

confidence: 99%

Conhydrine: An Account of Isolation, Biological Perspectives and Synthesis

2014

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Conhydrine is a naturally occurring 2-substituted piperidine alkaloid from the plant Conium maculatum L that exists in four different forms and is known for its high toxicity. This article focuses on the synthesis of conhydrine as its medicinal applications are limited due to its high toxicity. The various asymmetric methods developed for the synthesis of conhydrine are classified based on the methodology: the chiral pool method, the chiral auixiliary method, and asymmetric catalysis. A brief overview of the complete synthetic coverage of conhydrine in different isomeric forms is given.

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Section: Chiral Auxiliary Mediated Synthesismentioning

confidence: 99%

Conhydrine: An Account of Isolation, Biological Perspectives and Synthesis

2014

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“…12,13 Since then, several groups,including ours, have undertaken synthetic efforts to produce this compound, which appeared initially to be a novel, β2-selective nicotinic acetylcholine receptor agonist. 13–18 …”

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confidence: 99%

Epiquinamide: A Poison That Wasn’t from a Frog That Was

et al. 2009

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In 2003, we reported the isolation, structure elucidation, and pharmacology of epiquinamide, a novel alkaloid isolated from an Ecuadoran poison frog, Epipedobates tricolor. Since then, several groups, including ours, have undertaken synthetic efforts to produce this compound, which appeared initially to be a novel, β2-selective nicotinic acetylcholine receptor agonist. Based on chiral GC analysis of synthetic and natural samples, the absolute structure of this alkaloid is established as (1S, 9aS)-1-acetamidoquinolizidine. The synthetic epiquinamide is inactive at nicotinic receptors, in accord with recently published reports. However, the natural material retains activity that is not easily traced to known active components of the original extract. We report herein our results and possible reasons for this discrepancy.

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“…Thus, the high yielding and short asymmetric synthesis of (À)-a-conhydrine has been disclosed, 93 as well as the formal syntheses of (À)-epiquinamide and (À)-homopumiliotoxin 223G. 94 4.2.3.3 g-Amino alcohol derivatives. Either anti-or syng-amino alcohol derivatives can be synthetized by reduction of b-hydroxy tBS-imines 90 (the preparation of which is discussed in section 4.3) depending on the reducing agent used.…”

Section: Through Metal-catalyzed Additions Of Boronic Acidsmentioning

confidence: 99%

tert-Butanesulfinimines: structure, synthesis and synthetic applications

et al. 2009

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Since Ellman's seminal works, over the past ten years tert-butanesulfinimines have proved to be useful chiral amino intermediates for organic synthesis. Through highly stereoselective reactions, amongst which reductions, nucleophilic 1,2-additions and ylide condensations, a broad range of nitrogen-containing compounds has been synthesized. Although the stereoselectivity levels are high in most cases, the sense of the stereoinduction is generally not predictable. The object of this critical review is to present the models proposed to rationalize the stereochemical outcome of the reactions involving tert-butanesulfinimines and to point out an obvious lack of homogeneity amongst them (128 references).

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Asymmetric Synthesis of (−)-1-Hydroxyquinolizidinone, a Common Intermediate for the Syntheses of (−)-Homopumiliotoxin 223G and (−)-Epiquinamide

Abstract: The short and efficient asymmetric synthesis of (-)-1-hydroxyquinolizidinone was achieved in seven steps and 25.2% overall yield from readily available 5-chloropentanal. It is a key intermediate in the formal syntheses of (-)-homopumilotoxin 223G and (-)-epiquinamide.

Cited by 47 publications

References 20 publications

Conhydrine: An Account of Isolation, Biological Perspectives and Synthesis

Conhydrine: An Account of Isolation, Biological Perspectives and Synthesis

Epiquinamide: A Poison That Wasn’t from a Frog That Was

tert-Butanesulfinimines: structure, synthesis and synthetic applications

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