Synthesis of Strychnine

Bonjoch, Josep; Solé, Daniel

doi:10.1021/cr9902547

Cited by 317 publications

(98 citation statements)

References 132 publications

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“…[3,4] In chemistry, the intricate structure of strychnine has been a favorite target for organic synthesis. [5] It is a favored standard sample for NMR spectroscopy because of its availability, low cost, and the remarkable chemical shift dispersion of its 22 proton resonances. [6] Strychnine is usually obtained by acid-base extraction from seeds of the Strychnos nux vomica tree commonly grown in India.…”

Section: Introductionmentioning

confidence: 99%

Counterion influence on chemical shifts in strychnine salts

Metaxas

Cort

2013

Magnetic Reson in Chemistry

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The highly toxic plant alkaloid strychnine is often isolated in the form of the anion salt of its protonated tertiary amine. Here, we characterize the relative influence of different counterions on (1)H and (13)C chemical shifts in several strychnine salts in D2O, methanol-d4 (CD3OD), and chloroform-d (CDCl3) solvents. In organic solvents but not in water, substantial variation in chemical shifts of protons near the tertiary amine was observed among different salts. These secondary shifts reveal differences in the way each anion influences electronic structure within the protonated amine. The distributions of secondary shifts allow salts to be easily distinguished from each other as well as from the free base form. Slight concentration dependence in chemical shifts of some protons near the amine was observed for two salts in CDCl3, but this effect is small compared with the influence of the counterion. Distinct chemical shifts in different salt forms of the same compound may be useful as chemical forensic signatures for source attribution and sample matching of alkaloids such as strychnine and possibly other organic acid and base salts.

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Section: Introductionmentioning

confidence: 99%

Counterion influence on chemical shifts in strychnine salts

Metaxas

Cort

2013

Magnetic Reson in Chemistry

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“…1 As part of our ongoing interest in these classes of alkaloids, 2 we are particularly concerned with a synthesis of the core tetracyclic sub-structure 1, which forms the basis of these molecules as exemplified by strychnine 2 and aspidospermidine 3 ( Figure 1). Following the successful cyclisation of the N-pentenyl precursor 4 in our previous example, 3 we decided to use the same conditions for cyclisation of the N-pentynyl precursor 6.…”

Section: Introductionmentioning

confidence: 99%

The tandem radical route to indole alkaloids: an unusual rearrangement reaction

Hilton¹,

Jones²

2006

Arkivoc

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“…1 Their broad pharmacological indications in conjunction with their structural complexity allow this family of alkaloids to be under intense investigation. 2 Among the established catalytic enantioselective methods, reactions employing 3-alkylidene oxindoles are probably the most thoroughly studied. Taking advantage of the polarized α,β-unsaturated system, two major variants of spiroindoline syntheses, namely cycloaddition and annulation, have been achieved in a stereoselective manner and enantiomerically pure spirooxindoles were accessible by proper catalysis.…”

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confidence: 99%