aspidospermidine has been researched along with vincadifformine* in 6 studies
6 other study(ies) available for aspidospermidine and vincadifformine
| Article | Year |
|---|---|
Total Synthesis of (±)-Aspidospermidine, (±)-Aspidofractinine, (±)-Limaspermidine, and (±)-Vincadifformine via a Cascade and Common Intermediate Strategy.
A concise strategy for the total synthesis of several Topics: Alkaloids; Aspidosperma; Indole Alkaloids; Stereoisomerism | 2022 |
A unified synthesis of topologically diverse Aspidosperma alkaloids through divergent iminium-trapping.
Aspidospermidine, vincadifformine, 1,2-dehydroaspidospermidine, goniomitine, and quebrachamine, five Aspidosperma alkaloids distributed within three structurally diverse topologies, were synthesized from a single molecular scaffold, namely indole-valerolactam 6. This common intermediate can be divergently manipulated, through the incorporation of conformational and electronic constraints that influence the chemo-selectivity of the iminium ion derived therefrom, between three different reaction paths: N(1) vs. C(3) cyclization (indole numbering) vs. over-reduction. Moreover, a catalytic carbene insertion for direct C(3)-H indole functionalization is reported for the first time in an approach to goniomitine (4), and a following tandem ester reduction/iminium generation/cyclization secured its tetracyclic system. The development of a highly diastereoselective one-pot hemi-reduction/cyclization/deprotection process to obtain a cis-pyridocarbazole directly allowed the synthesis of pentacyclic Aspidosperma alkaloids 1, 2, and 3. Topics: Alkaloids; Aspidosperma; Chemistry Techniques, Synthetic; Cyclization; Indole Alkaloids; Quinolines; Stereoisomerism | 2018 |
Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (-)-Aspidospermidine, (-)-Tabersonine, and (-)-Vincadifformine.
The development and application of the arene-fused domino Michael/Mannich route to the tetrahydrocarbazole (ABE) core of Aspidosperma alkaloids is described. The scope of this novel transformation was studied in terms of the nucleophilic component (i.e., N-sulfinyl metallodienamine) and the electrophilic component (i.e., Michael acceptor). The successful application of this methodology toward the concise total syntheses of classical indole alkaloids (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine in 10-11 steps, respectively, is also discussed. Topics: Alkaloids; Indole Alkaloids; Molecular Structure; Quinolines; Stereoisomerism | 2017 |
Unified strategy to monoterpene indole alkaloids: total syntheses of (±)-goniomitine, (±)-1,2-dehydroaspidospermidine, (±)-aspidospermidine, (±)-vincadifformine, and (±)-kopsihainanine A.
Total syntheses of (±)-goniomitine, (±)-1,2-dehydroaspidospermidine, (±)-aspidospermidine, (±)-vincadifformine, and (±)-kopsihainanine A were achieved featuring two common key steps: (1) a palladium-catalyzed decarboxylative vinylation that provides quick access to cyclopentene intermediates containing all of the carbons present in the natural products and (2) an integrated oxidation/reduction/cyclization (iORC) sequence for skeletal reorganization that converts the cyclopentenes to the pentacyclic structures of the natural products. By incorporation of a geometric constraint to iORC substrates, both the chemoselectivity (C7 vs N1 cyclization) and the stereoselectivity (trans- vs cis-fused ring system) of the cyclization process can be controlled. Topics: Alkaloids; Biological Products; Chemistry Techniques, Synthetic; Heterocyclic Compounds, 4 or More Rings; Indole Alkaloids; Monoterpenes; Quinolines | 2014 |
Domino Michael/Mannich/N-alkylation route to the tetrahydrocarbazole framework of aspidosperma alkaloids: concise total syntheses of (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine.
We report a novel, asymmetric domino Michael/Mannich/N-alkylation sequence for the rapid assembly of the tetrahydrocarbazole framework of Aspidosperma alkaloids. This method was utilized in the concise total syntheses of classical targets (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine in 10 or 11 steps. Additional key steps include ring-closing metathesis to prepare the D-ring and Bosch-Rubiralta spirocyclization to prepare the C-ring. Topics: Alkaloids; Alkylation; Aspidosperma; Carbazoles; Indole Alkaloids; Molecular Structure; Quinolines; Stereoisomerism | 2013 |
Collective synthesis of natural products by means of organocascade catalysis.
Organic chemists are now able to synthesize small quantities of almost any known natural product, given sufficient time, resources and effort. However, translation of the academic successes in total synthesis to the large-scale construction of complex natural products and the development of large collections of biologically relevant molecules present significant challenges to synthetic chemists. Here we show that the application of two nature-inspired techniques, namely organocascade catalysis and collective natural product synthesis, can facilitate the preparation of useful quantities of a range of structurally diverse natural products from a common molecular scaffold. The power of this concept has been demonstrated through the expedient, asymmetric total syntheses of six well-known alkaloid natural products: strychnine, aspidospermidine, vincadifformine, akuammicine, kopsanone and kopsinine. Topics: Alkaloids; Biological Products; Biomimetics; Catalysis; Chemistry, Organic; Cyclization; Indole Alkaloids; Indoles; Quinolines; Research Design; Strychnine | 2011 |