Stereoselective synthesis of methyl 3α-ethyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-1α-carboxylate: A key intermediate for the preparation of tacamine-type indole alkaloids

doi:10.1016/0040-4039(96)00052-4

Paper

DOI: 10.1016/0040-4039(96)00052-4

Stereoselective synthesis of methyl 3α-ethyl-1,2,3,4,6,7,12,12bβ-octahydroindolo[2,3-a]quinolizine-1α-carboxylate: A key intermediate for the preparation of tacamine-type indole alkaloids

Published Feb 26, 1996 · M. Lounasmaa, Kimmo Karinen, D. Belle

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Methyl 3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-carboxylate is a key intermediate for the synthesis of tacamine-type indole

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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References

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Tetrahedron Letters

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Asymmetric total synthesis of tacamonine (pseudovincamone I) via radical cyclization

Tacamonine (1) was synthesized by radical cyclization of piperidinone (18) with (-)-(2S)-2-(tert-Butyldimethylsilyloxy)methyl)butan-1-ol (6), resulting in a diastereomeric mixture of

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Total Synthesis of the Indole Alkaloid ()-Tacamine

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Tetrahedron Letters

DOI: 10.1002/HLCA.19940770314

Aldehyde Intermediates in the Synthesis of Tacamine‐Type Indole Alkaloids: Preparation of (±)‐apotacamine

This study demonstrates a simple, efficient method for synthesising tacamine-type indole alkaloids, leading to the preparation of ()-apotacamine.

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Substrate induced diastereoselective hydrogenation/reduction of arenes and heteroarenes

This method allows the preparation of chiral, racemic or optically pure, substituted cyclohexanes, piperidines, tetrahydrofurans, and pyrrolidines by diastereoselective hydrogenation/reduction of aromatic and heteroaromatic precursors,

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New Route to 20-Deethyldasycarpidone by Ring-Closure with DDQ

This study presents a new route to 20-deethyldasycarpidone (8) in 21% overall yield from 1,2,3,4-tetrahydrocarbazol-1-one (1), a key Strychnos alkaloid with potential pharmaceutical applications.

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Annulated 1,2,3,4-tetrahydro-β-carbolines by intramolecular Mannich-type amino- and amidoalkylations of N(9)-(ω-nitroalkyl)-3,4-dihydro-β-carbolines

This study successfully transformed 2-[1-(ω-Nitroalkyl)-1H-indol-3-yl]ethylformamides into annulated tetrahydro-β-carbolines and tetracyclic diazacycloalkano[jk]fluorenes, with potential applications in drug development.

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Tetrahedron

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Acid-catalysed epimerization of indolo[2,3-a]quinolizidines. 1-, 2- and 3-monosubstituted alkyl derivatives

Acid-catalyzed epimerization of indolo[2,3-a]quinolizidines in refluxing TFA leads to an equilibrium mixture of C-12b diastereomers, offering a new stereoselective synthesis of 2-ethylindolo[2,3-

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Tetrahedron

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Acid-catalysed epimerization of 1-substituted indolo[2,3-a]quinolizidines: Stereoselective routes to cis- and trans-deethyleburnamonine starting from the same ester intermediate

Acid-catalyzed epimerization of 1-substituted indolo[2,3-a]quinolizidines allows efficient syntheses of pharmacologically interesting deethyleburnamonines 2 and 3 from the same ester intermediate.

1996·13citations·M. Lounasmaa et al.·Tetrahedron

Tetrahedron