171256-40-9

Upstream product

• 136057-11-9 dimethyl (2S,3aR,8aS)-8-benzenesulphonyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-1,2-dicarboxylate 
• 79465-82-0 L-(2β,3aα,8aα)-1,2,3,3a,8,8a-hexahydro-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole 
• 66377-68-2 N-(methoxycarbonyl)-L-tryptophan methyl ester 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 

Downstream Products

• 709030-59-1 (2R,3aR,8aS)-8-benzenesulfonyl-2-phenylselenyl-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester 
• 709030-61-5 (2R,3aR,8aS)-2-allyl-8-benzenesulfonyl-3,3a,8,8a-hexahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester 
• 1333120-78-7 C₂₃H₂₆N₂O₆S 
• 1333120-83-4 C₃₆H₄₇N₃O₉S 
• 1356557-85-1 C₄₈H₅₉N₅O₁₁S 

Relevant academic research and scientific papers

Orthogonal protecting groups in the synthesis of tryptophanyl- hexahydropyrroloindoles

The synthesis of various polycyclic systems containing aC 3a-Ni bond between a hexahydropyrrolo[2,3-b]indole and an indole tryptophan is described here. A series of experiments were performed to determine the best combination of five orthogonal protecting groups and the best reaction conditions for formation of said bond, which is a common feature among many recently discovered marine natural products.

Concise, stereocontrolled synthesis of the citrinadin B core architecture

A concise, stereocontrolled synthesis of the citrinadin B core architecture from scalemic, readily available starting materials is disclosed. Highlights include ready access to both cyclic tryptophan tautomer and trans-2,6- disubstituted piperidine fragme

Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine

Conjoined twins: An efficient and convergent strategy for the synthesis of the dimeric hexahydropyrroloindole alkaloids, (+)-chimonanthine, (+)-folicanthine, and (-)-calycanthine, is described. The simultaneous formation of the vicinal quaternary stereocenters by using a reductive dimerization reaction provides an access to the optically active key intermediate on a gram scale. (Chemical Equation Presented).