6879-55-6

Upstream product

• 50-00-0 formaldehyd 
• 1356938-38-9 1,2,3,3a,8,8a-hexahydro-3a-(1,2,3,3a,8,8a-hexahydro-8-methylpyrrolo[2,3-b]indol-3a-yl)-8-methylpyrrolo[2,3-b]indole 
• 73-22-3 L-Tryptophan 
• 4299-70-1 L-tryptophan methyl ester 
• 1064604-21-2 methyl (2S,3aR,8aR)-[3a-bromo-(1,2,3,3a,8,8a)-hexahydropyrrolo[2,3-b]indole-1,8-di-tertbutoxycarbonyl]-2-carboxylate 
• 96238-68-5 tert-butyl (+)-(S)-3-[2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropyl]-1H-indole-1-carboxylate 
• 1629094-37-6 dimethyl (-)-(2S,2'S,3aS,3'aS,8aR,8'aR)-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2'-dicarboxylate 
• 1629094-40-1 dimethyl (-)-(2S,2'S,3aS,3'aS,8aR,8'aR)-1,1',8,8'-tetramethyl-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-3a,3'a-bipyrrolo[2,3-b]indole-2,2'-dicarboxylate 
• 1566578-26-4 (3S,3'S)-3,3'-diallyl-1,1'-dimethyl-[3,3'-biindoline]-2,2'-dione 
• 1380315-88-7 di-tert-butyl 2,2′-dioxo-[3,3′-biindoline]-1,1′-dicarboxylate 

Relevant academic research and scientific papers

C-H functionalization/asymmetric michael addition cascade enabled by relay catalysis: Metal carbenoid used for C-C bond formation

A combination of either ruthenium(II) or rhodium(II) complexes and quinine-derived squaramide enables 3-diazooxindoles, indoles, and nitroalkenes to undergo highly efficient asymmetric three-component reactions, thus affording optically active 3,3′-bis(in

Dielectrophilic Allenic Ketone-Enabled [4 + 2] Annulation with 3,3'-Bisoxindoles: Enantioselective Creation of Two Contiguous Quaternary Stereogenic Centers

We introduced a type of allenic ketone as a dielectrophilic C4 synthon in phosphine-mediated reactions. The high electrophilicity of the advanced intermediates created upon phosphine activation empowered the utilization of 3,3′-bis-oxindoles as a two-carbon reaction partner in a highly enantioselective [4 + 2] annulation, allowing for facile creation of spirocyclic bisindoline structures containing two contiguous quaternary stereogenic centers. Synthetic manipulations of the [4 + 2] annulation product led to concise total synthesis of (-)-folicanthine.

Catalytic Enantioselective Decarboxylative Allylations of a Mixture of Allyl Carbonates and Allyl Esters: Total Synthesis of (-)- and (+)-Folicanthine

A highly enantioselective decarboxylative allylation of a mixture of enol carbonates and allyl esters has been achieved. The strategic viability of this methodology has been demonstrated through the total synthesis of cyclotryptamine alkaloids (-)- and (+)-folicanthine (1 a) and the formal total synthesis of (-)-chimonanthine (1 b), (+)-calycanthine (1 c), and (-)-ditryptophenaline (1 d).

Unified synthesis of (-)-folicanthine and (-)-ditryptophenaline enabled by a room temperature nickel-mediated reductive dimerization

A Ni·Phen-mediated reductive homocoupling of an optically active tertiary bromide has been efficiently achieved after the systematic screen of reaction conditions including ligands. This key step establishes sterically hindered vicinal quaternary stereocenters embedded in natural bispyrrolo[2,3-b]indoline alkaloids, thus enabling to realize the first asymmetric total synthesis of (-)-folicanthine via the detailed investigation of a challenging double decarboxylation. Notably, the concise synthesis of diketopiperazine alkaloid (-)-ditryptophenaline was also completed from the common dimeric intermediate. Georg Thieme Verlag Stuttgart New York.

Iodine-mediated regioselective C2-amination of indoles and a concise total synthesis of (±)-folicanthine

Highly substituted 2-aminated indoles can be prepared in moderate to excellent yields by regioselective C2-amination of indoles promoted by iodine. As a key step in a concise synthesis of (±)-folicanthine, its core structure was easily obtained by one step cyclization-dimerization of substituted tryptophan in high yield on a gram scale. The Royal Society of Chemistry.