Chapter 17 Strychnos Alkaloids

Smith, George F.

doi:10.1016/s1876-0813(08)60056-1

Cited by 12 publications

(8 citation statements)

References 135 publications

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“…The structure elucidation of strychnine has been welldocumented in several excellent review articles by R. Huisgen (1951), 11 G. F. Smith (1965) 12 L. B. Slater (2001), 13 and J. I. Seeman, D. J. Tantillo (2020).…”

Section: Introductionmentioning

confidence: 92%

“…However, its basicity (pK a 3.8) is much lower than that of a conventional enamine because protonation on the b-carbon (C21) would lead to an unfavorable bridgehead N19]C20 double bond. 12 Substitution reactions at C11 of strychnine are shown in Scheme 3. The C11 methylene group is CH-acidic and undergoes condensation reactions with aromatic aldehydes exemplied by the formation of 11-benzylidene strychnine (28).…”

Section: Oxidation and Non-aromatic Substitution Productsmentioning

confidence: 99%

“…However, its basicity (p K a 3.8) is much lower than that of a conventional enamine because protonation on the β-carbon (C21) would lead to an unfavorable bridgehead N19C20 double bond. 12…”

Section: Natural and Synthetic Monomeric Strychnine Analoguesmentioning

confidence: 99%

“…The structure elucidation of strychnine has been well-documented in several excellent review articles by R. Huisgen (1951), 11 G. F. Smith (1965) 12 L. B. Slater (2001), 13 and J. I. Seeman, D. J. Tantillo (2020). 14 Given the complex constitution of strychnine, it is not surprising that it took almost 130 years from its isolation in pure form in 1818 until its accurate molecular structure was revealed.…”

Section: Introductionmentioning

confidence: 96%

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Strychnine and its mono- and dimeric analogues: a pharmaco-chemical perspective

Zlotos

Mandour²,

Jensen

2022

Nat. Prod. Rep.

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Section: Introductionmentioning

confidence: 92%

Section: Oxidation and Non-aromatic Substitution Productsmentioning

confidence: 99%

Section: Natural and Synthetic Monomeric Strychnine Analoguesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 96%

See 2 more Smart Citations

Strychnine and its mono- and dimeric analogues: a pharmaco-chemical perspective

Zlotos

Mandour²,

Jensen

2022

Nat. Prod. Rep.

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“…Conflicting results during the chemical characterization of ipecoside (I) indicated (Smith, 1969) that inversion at C(13) had occurred at some stage. An X-ray study was undertaken to resolve this question by determining the molecular geometry and absolute configuration.…”

Section: Introductionmentioning

confidence: 99%

The crystal structure and absolute configuration of O,O-dimethylipecoside

Roberts¹,

Isaacs²,

Allen³

et al. 1974

Acta Crystallogr Sect B

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O,O‐Dimethylipecoside is orthorhombic, space group C2221, with a = 29.57 (3), b = 825 (1), c = 29.52 (3) Å, Z = 8. The structure was solved by tangent formula refinement of diffractometer data collected with Cu radiation. Full‐matrix least‐squares refinement resulted in a final R of 0.141 for 2159 reflexions. The dihydroisoquinoline ring has the expected geometry. The dihydropyranyl ring is a ‘half‐chair’ and the glucose ring is in the chair form. The absolute configuration was assigned from the knowledge that hydrolysis of ipecoside yields d‐glucose.

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Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine

Zhao

Teijaro

Chen

et al. 2016

Chemistry A European J

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The first chemical syntheses of complex, bis-Strychnos alkaloids (-)-sungucine (1), (-)-isosungucine (2), and (-)-strychnogucine B (3) from (-)-strychnine (4) is reported. Key steps included (1) the Polonovski-Potier activation of strychnine N-oxide; (2) a biomimetic Mannich coupling to forge the signature C23-C5' bond that joins two monoterpene indole monomers; and (3) a sequential HBr/NaBH3 CN-mediated reduction to fashion the ethylidene moieties in 1-3. DFT calculations were employed to rationalize the regiochemical course of reactions involving strychnine congeners.

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Chapter 17 Strychnos Alkaloids

Cited by 12 publications

References 135 publications

Strychnine and its mono- and dimeric analogues: a pharmaco-chemical perspective

Strychnine and its mono- and dimeric analogues: a pharmaco-chemical perspective

The crystal structure and absolute configuration of O,O-dimethylipecoside

Concise Syntheses of bis‐Strychnos Alkaloids (−)‐Sungucine, (−)‐Isosungucine, and (−)‐Strychnogucine B from (−)‐Strychnine

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