150881-27-9

Basic information

• Product Name: [10b,10'b-Bi-10bH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone,2,2',3,3',5a,5'a,6,6',11,11',11a,11'a-dodecahydro-3,3'-bis(phenylmethyl)-,(3S,3'S,5aR,5'aR,10bR,10'bR,11aS,11'aS)-
• Synonyms: Chaetocin,2,5:2',5'-dide(epidithio)-3,3'-didemethyl-19,19'-dideoxy-19,19'-diphenyl-, (2a,2'b,5b,5'a)-;10bH-Pyrazino[1',2':1,5]pyrrolo[2,3-b]indole, chaetocin deriv.; (+)-Win 64821;Q 20547A; Win 64821; [10b,10'b-Bi-10bH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone,2,2',3,3',5a,5'a,6,6',11,11',11a,11'a-dodecahydro-3,3'-bis(phenylmethyl)-,[3S-[3a,5ab,10bb(3'R*,5'aS*,10'bS*,11'aR*),11ab]]-
• CAS NO: 150881-27-9
• Molecular Formula: C40H36 N6 O4
• Molecular Weight: 664.764
• Mol File: 150881-27-9.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.48g/cm³
• CAS DataBase Reference: [10b,10'b-Bi-10bH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone,2,2',3,3',5a,5'a,6,6',11,11',11a,11'a-dodecahydro-3,3'-bis(phenylmethyl)-,(3S,3'S,5aR,5'aR,10bR,10'bR,11aS,11'aS)-(CAS DataBase Reference)
• NIST Chemistry Reference: [10b,10'b-Bi-10bH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone,2,2',3,3',5a,5'a,6,6',11,11',11a,11'a-dodecahydro-3,3'-bis(phenylmethyl)-,(3S,3'S,5aR,5'aR,10bR,10'bR,11aS,11'aS)-(150881-27-9)
• EPA Substance Registry System: [10b,10'b-Bi-10bH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone,2,2',3,3',5a,5'a,6,6',11,11',11a,11'a-dodecahydro-3,3'-bis(phenylmethyl)-,(3S,3'S,5aR,5'aR,10bR,10'bR,11aS,11'aS)-(150881-27-9)

Safety Data

• Hazardous Substances Data: 150881-27-9(Hazardous Substances Data)

Upstream product

• 1014106-95-6 C₅₂H₄₄N₆O₈S₂ 
• 1051926-24-9 (2S,2'S,3aR,3a'R,8aS,8a'S)-2,3,8,8a,2',3',8',8a'-octahydro-1H,1'H-[3a,3a']-bi[pyrrolo[2,3-b]indolyl]-2,2'-dicarboxylic acid dimethyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 1512867-54-7 C₅₂H₆₀N₆O₁₀ 
• 1161-13-3 N-Cbz-L-Phe 
• 73-22-3 L-Tryptophan 
• 856865-61-7 N-(o-nitrobenzenesulfonyl)-L-tryptophan methyl ester 
• 1051926-23-8 dimethyl (2S,2'S,3aR,3'aR,8aR,8'aR)-1,1'-bis(((benzyloxy)carbonyl)-L-phenylalanyl)-2,2',3,3',8,8a,8',8'a-octahydro-1H,1'H-[3a,3'a-bipyrrolo[2,3-b]indole]-2,2'-dicarboxylate 
• 1051926-27-2 (2S,2'S,3aR,3a'R,8aR,8a'R)-1,1'-bis-((S)-2-amino-3-phenyl-propionyl)-2,3,8,8a,2',3',8',8a'-octahydro-1H,1'H-[3a,3a']-bi[pyrrolo[2,3-b]indolyl]-2,2'-dicarboxylic acid dimethyl ester 
• 7479-05-2 L-tryptophan ethyl ester 

Relevant articles and documents

Collective synthesis and biological evaluation of tryptophan-based dimeric diketopiperazine alkaloids

A concise two one-pot synthesis of WIN 64821, eurocristatine, 15,15′-bis-epi-eurocristatine, ditryptophenaline, ditryptoleucine A, WIN 64745, cristatumin C, asperdimin, naseseazine A, and naseseazine B is detailed, based on a unique bioinspired dimerization reaction of tryptophan derivatives in aqueous acidic solution and a one-pot procedure for the construction of diketopiperazine rings. Total yields of these alkaloid syntheses were from 10 up to 27 %. In addition, 1′-(2-phenylethylene)-ditryptophenaline was synthesized by using three one-pot operations. The studies detailed herein provided synthesized natural products for inhibitory activities of ubiquitin-specific protease 7 (USP7) and foam cell formation in macrophages. The newly listed biological evaluation for tryptophan-based dimeric diketopiperazine alkaloids discovered 15,15′-bis-epi-eurocristatine, 1′-(2-phenylethylene)-ditryptophenaline, and WIN 64745 as new drug candidates. All in one: A concise synthesis of tryptophan-based dimeric diketopiperazine alkaloids (see scheme) is detailed based on a unique bioinspired dimerization reaction of tryptophan derivatives and a one-pot procedure for construction of diketopiperazine rings. Some of the synthetic alkaloids were discovered as new drug candidates for cancer or atherosclerosis therapy.

Bio-inspired dimerization reaction of tryptophan derivatives in aqueous acidic media: Three-step syntheses of (+)-WIN 64821, (-)-ditryptophenaline, and (+)-naseseazine B

Doubling up: The direct bio-inspired dimerization of commercially available amine-free tryptophan derivatives in aqueous acidic media provides C 2-symmetrical and nonsymmetrical dimeric compounds. Further processing completes the concise synthe

Nickel-catalyzed dimerization of pyrrolidinoindoline scaffolds: Systematic access to chimonanthines, folicanthines and (+)-WIN 64821

While metal-promoted activation of tertiary alkyl halides often causes elimination and hydrodehalogenation, we have developed a nickel-catalyzed reductive dimerization that allows the generation of a potently reactive tertiary radical equivalent to form a very congested C(sp3)-C(sp 3) bond even below room temperature. The catalytic protocol is applicable to the dimerization of several pyrrolidinoindoline scaffolds through an appropriate choice of catalyst to accommodate different substrate reactivities with functional group compatibilities. The efficiency of the nickel-catalyzed protocol was successfully demonstrated through a systematic total synthesis of chimonanthines, folicanthines and (+)-WIN 64821.

Exploration of a KI-catalyzed oxidation system for direct construction of bispyrrolidino[2,3-: B] indolines and the total synthesis of (+)-WIN 64821

A facile and environmentally benign KI(cat.)/NaBO3·4H2O oxidation system has been developed for the tandem oxidative aminocyclization/coupling of tryptamines, affording a series of 3a,3a′-bispyrrolidino[2,3-b]indolines with high efficiency (up to 94% yield). This reaction features an electrophilic "I+" mechanism, which is importantly quite different from and milder than the typical radical-involving process, and can be readily amplified for the total synthesis of (+)-WIN 64821.

Copper-mediated dimerization to access 3a,3a′-bispyrrolidinoindoline: Diastereoselective synthesis of (+)-WIN 64821 and (-)-ditryptophenaline

A copper-mediated cyclization and dimerization of tryptamine or tryptophan was developed to generate a C2-symmetry C3(sp3)-C3(sp3) bridge with two contiguous stereogenic quaternary carbons in one step. Impressively, the ratio between exo and endo cyclization products varies when different protecting groups of Nb are utilized. This dimerization reaction could be conducted in gram scale. With this dimerization method, both endocyclotryptophan (+)-WIN 64821 and exocyclotryptophan (-)-ditryptophenaline were synthesized in 5 steps.

Stereocontrolled and versatile total synthesis of bispyrrolidinoindoline diketopiperazine alkaloids: structural revision of the fungal isolate (+)-Asperdimin

Homo- and heterodimeric bispyrrolidinoindoline diketopiperazine alkaloids have been synthesized following a concise, versatile, and stereoselective route. Highlights of the sequence are a diastereoselective construction of the C3a-bromo-hexahydropyrrolo[2

Concise total synthesis of (+)-WIN 64821 and (-)-ditryptophenaline

(Chemical Equation Presented) On a fast track: The secondary metabolites (+)-WIN 64821 and (-)-ditryptophenaline have been synthesized in six and seven steps, respectively, from amino acid derivatives in a concise and enantioselective manner. The gram-scale synthesis of key intermediates and the simultaneous introduction of vicinal quaternary stereocenters are described. The synthesis and structural confirmation of (-)-1′-(2-phenylethylene) ditryptophenaline is also reported.