Vobasine, vincamine, voaphylline, tacaman, and iboga alkaloids from Tabernaemontana corymbosa

Sim, Dawn Su-Yin; Tang, Sin-Yee; Low, Yun‐Yee; Lim, Siew‐Huah; Kam, Toh‐Seok

doi:10.1016/j.phytochem.2022.113384

Cited by 4 publications

(3 citation statements)

References 33 publications

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“…This hasubanan-type alkaloid is dimethyl-acutuminine . A Malaysian collection of Tabernaemontana corymbosa , a widely distributed plant and well-known repository of indole alkaloids, yields 13 undescribed alkaloids, including the chlorine-containing voafinisine B ( 328 ) …”

Section: Terrestrial Plantsmentioning

confidence: 99%

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

Gribble

2024

J. Nat. Prod.

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The discovery of naturally occurring organohalogen compounds has increased astronomically in the 55 years since they were first discovered�from fewer than 50 in 1968 to a combined 7,958 described examples in three comprehensive reviews. The present survey, which covers the period 2021−2023, brings the number of known natural organohalogens to approximately 8,400. The organization is according to species origin, and coverage includes marine and terrestrial plants, fungi, bacteria, marine sponges, corals, cyanobacteria, tunicates, and other marine organisms.

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Section: Terrestrial Plantsmentioning

confidence: 99%

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

Gribble

2024

J. Nat. Prod.

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“…There are several reports on the synthesis of alkyl pyrralines. − Alkylation of pyrrole derivatives is known to be a simple and reliable reaction, although strong basic conditions are generally used. However, it has been reported that the epimerization of the methyl ester on the vobasine skeleton proceeds readily under basic conditions . On the basis of the above, we planned to synthesize the pyrraline skeleton using a pyranone derivative 2 , which proceeds under weakly acidic conditions in the late stage of the synthesis.…”

mentioning

confidence: 99%

“…However, it has been reported that the epimerization of the methyl ester on the vobasine skeleton proceeds readily under basic conditions. 5 On the basis of the above, we planned to synthesize the pyrraline skeleton using a pyranone derivative 2 , which proceeds under weakly acidic conditions in the late stage of the synthesis. The regioselectivity and stereoselectivity of the introduction of the tryptamine derivative in the vobasine skeleton must be controlled, and we speculated that the regioselectivity of the tryptamine derivative would be C2-selective on the basis of its electron density.…”

mentioning

confidence: 99%