107673-22-3

Upstream product

• 100-63-0 phenylhydrazine 
• 1037-83-8 C₁₉H₂₂N₂O 
• 125947-55-9 1-[(6aS,11bS)-3-(3-Allyloxy-propyl)-7-benzyl-2,3,5,6,6a,7-hexahydro-1H-pyrrolo[2,3-d]carbazol-4-yl]-ethanone 
• 125947-52-6 1-[(3aS,6aS,11bS)-3-(3-Allyloxy-propyl)-7-benzyl-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo[2,3-d]carbazol-4-yl]-ethanone 
• 125947-54-8 (6aS,11bS)-3-(3-Allyloxy-propyl)-7-benzyl-5,6,6a,7-tetrahydro-3H-pyrrolo[2,3-d]carbazol-2-one 
• 125947-56-0 1-((3aR,5aS,10bS,12bR)-6-Benzyl-2,3,4,5,5a,6,11,12-octahydro-1H-6,12a-diaza-indeno[7,1-cd]fluoren-3a-yl)-ethanone 
• 125947-57-1 20-oxoaspidospermidine 
• 129593-07-3 1-((3aS,6aR,11bR)-7-Acetyl-3-benzyl-2,3,3a,4,5,6,6a,7-octahydro-1H-pyrrolo[2,3-d]carbazol-4-yl)-ethanone 
• 129593-08-4 1-((3aS,6aR,11bS)-4-Acetyl-1,2,3,3a,4,5,6,6a-octahydro-pyrrolo[2,3-d]carbazol-7-yl)-ethanone 
• 99459-02-6 9-benzyl-1,2,3,4a,9,9a-hexahydrocarbazol-4-one 
• 129593-06-2 1-((6aR,11bR)-7-Acetyl-3-benzyl-2,3,5,6,6a,7-hexahydro-1H-pyrrolo[2,3-d]carbazol-4-yl)-ethanone 
• 129593-12-0 3-Chloro-1-((3aR,6aS,11bS)-4,7-diacetyl-1,2,3a,4,5,6,6a,7-octahydro-pyrrolo[2,3-d]carbazol-3-yl)-propan-1-one 
• 129593-02-8 (3aS,6aR,11bR)-3,7-Dibenzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one 
• 129593-03-9 (3aR,6aS,11bS)-3-Benzyl-3a-hydroxy-3a,4,5,6,6a,7-hexahydro-3H-pyrrolo[2,3-d]carbazol-2-one 

Downstream Products

• 6871-25-6 (+/-)-aspidofractinine 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF (+/-) ASPIDOFRACTININE

The pentacyclic skeleton 10 of the aspidospermine group of indole alkaloids has been constructed from hexahydrocarbazol-4-one 2 with high stereoselectivity.The synthesis of (+/-) 19-oxo aspidofractinine 12, a direct precursor of aspidofractinine 4, illustrates the usefulness of this new general strategy.

Total Syntheses of (?)-Minovincine and (?)-Aspidofractinine through a Sequence of Cascade Reactions

We report 8-step syntheses of (?)-minovincine and (?)-aspidofractinine using easily available and inexpensive reagents and catalyst. A key element of the strategy was the utilization of a sequence of cascade reactions to rapidly construct the penta- and hexacyclic frameworks. These cascade transformations included organocatalytic Michael-aldol condensation, a multistep anionic Michael-SN2 cascade reaction, and Mannich reaction interrupted Fischer indolization. To streamline the synthetic routes, we also investigated the deliberate use of steric effect to secure various chemo- and regioselective transformations.

Total Syntheses of Dihydroindole Aspidosperma Alkaloids: Reductive Interrupted Fischer Indolization Followed by Redox Diversification

We report a novel reductive interrupted Fischer indolization process for the concise assembly of the 20-oxoaspidospermidine framework. This rapid complexity generating route paves the way toward various dihydroindole Aspidosperma alkaloids with different C-5 side chain redox patterns. The end-game redox modulations were accomplished by modified Wolff-Kishner reaction and photo-Wolff rearrangement, enabling the total synthesis of (-)-aspidospermidine, (-)-limaspermidine, and (+)-17-demethoxy-N-acetylcylindrocarine and the formal total synthesis of (-)-1-acetylaspidoalbidine.

Total Synthesis of Indole Alkaloids. A New Strategy for (+/-)-19-Oxoaspidospermidine and (+/-)-19-Oxoaspidofractinine

A synthesis for the preparation of 19-oxoaspidospermidine (1) and 19-oxoaspidofractinine (2) has been developed beginning with tetracyclic amido alcohol 9.Dehydration of 9 gave enamine 10.Reduction to the corresponding enamine followed by reaction with ac

APPLICATION OF THE NEW ACYLATING AGENTS TO THE SYNTHESIS OF INDOLE ALKALOIDS. A TOTAL SYNTHESIS OF (+/-)-ASPIDOFRACTININE

The new acylating agents were proved to be useful for introduction of an acetyl group into the α-position of the carbonyl group by means of two-carbon Michael acceptors, which was successfully applied to