182234-25-9

Upstream product

• 599185-52-1 (2S,3S,5aS,10aS)-1',2',5a,6,7,8,10,10a-octahydro-6'-methoxy-3-(2-methoxy-2-methylpropyl)-2',5,10-trioxospiro[1H,5H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole] 
• 67-56-1 methanol 
• 807611-17-2 6-bromodemethoxyspirotryprostatin A 
• 599185-57-6 (2S,3S,5aS,10aR)-1',2',5a,6,7,8,10,10a-octahydro-6'-methoxy-3-(2-methoxy-2-methylpropyl)-2',5,10-trioxospiro[1H,5H-dipyrrolo[1,2-a:1',2'-d]pyrazine-2(3H),3'-[3H]indole] 
• 1031727-28-2 6-Methoxyspirotryprostatin B 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 208761-41-5 C₂₂H₂₅N₃O₄ 
• 181134-54-3 3-methoxy-3-methylbutanal 
• 225110-81-6 (2'S,3'S,5'S)-2'-(2-Methyl-allyl)-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-5'-carboxylic acid methyl ester 
• 208761-39-1 C₂₈H₃₁N₃O₄S 
• 111427-84-0 3-methyl-3-(phenylthio)butanal 
• 599185-51-0 (3S,3'S,4'R,6'S,8'aR)-1,2,3',4',8',8'a-hexahydro-6-methoxy-6'-(2-methoxy-2-methylpropyl)-1',2-dioxo-3',4'-diphenylspiro[3H-indole-3,7'(6'H)-[1H]pyrrolo[2,1-c][1,4]-oxazine] 
• 599185-55-4 (2'S,3S,5'R)-1,2-dihydro-6-methoxy-2'-(2-methoxy-2-methylpropyl)-2-oxospiro[3H-indole-3,3'-pyrrolidine]-5'-carboxylic acid 
• 599185-53-2 3-hydroxy-6-methoxy-3-trimethylsilyl-1,3-dihydroindol-2-one 

Relevant academic research and scientific papers

A concise synthesis of spirotryprostatin A

(Chemical Equation Presented) The preparation of two new synthons, 2,5- and 2,6-dibromotryptophan esters, and their use in diastereoselective intramolecular N-acyliminium ion spirocyclization methodology for the rapid construction of spirotryprostatin A and analogues are described.

Total Synthesis of Spirotryprostatins through Organomediated Intramolecular Umpolung Cyclization

Cyclodipeptide 2,5-diketopiperazines (DKP) are privileged structural units present in drugs and natural alkaloids. This work reports a new method for the synthesis of biologically important DKP scaffolds based on an intramolecular nucleophilic α-addition of general amides towards an alkynamide system. The utility of this umpolung cyclization mediated by trimethyl phosphine and l-glutamic acid is highlighted by its application to the concise total syntheses of 6-methoxyspirotryprostatin B (the first total synthesis), spirotryprostatin A, and spirotryprostatin B.

Catalytic bimetalic [Pd(0)/Ag(I) Heck-1,3-dipolar cycloaddition cascade reactions accessing spiro-oxindoles. Concomitant in situ generation of azomethine ylides and dipolarophile

Spiro-oxindoles, epi-Spirotryprostatin A and its analogues were prepared from a tactical combination of cascade catalytic bimetallic Pd (0)/Ag(I), intramolecular Heck and subsequent imine → azomethine ylide → 1,3-Dipolar cycloaddition reactions. The casca

Asymmetic organocatalytic 1,3-dipolar cycloaddition of azomethine ylide to methyl 2-(2-nitrophenyl)acrylate for the synthesis of diastereoisomers of spirotryprostatin A

Chemical equations presented. The total synthesis of two diastereomers of spirotryprostatin A has been established starting with an asymmetric 1,3-dipolar cycloaddition of methyl 2-(2-nitrophenyl)acrylate with azomethine ylides catalyzed by a Bronsted aci

Concise, asymmetric total synthesis of spirotryprostatin A

The structurally intriguing cell-cycle inhibitor spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived oxindole moiety that

Concise, asymmetric total synthesis of spirotryprostatin A

(Matrix presented) The structurally intriguing cell-cycle inhibitor spirotryprostatin A has been synthesized utilizing an azomethine ylide dipolar cycloaddition reaction as the key step. This pentacyclic alkaloid contains a prenylated tryptophan-derived o

Total synthesis of spirotryprostatin a, leading to the discovery of some biologically promising analogues

The total synthesis of the title compound has been accomplished. A key step involves the oxidative rearrangement of the β-carboline derivative to an oxindole via the action of N-bromosuccinimide. From this point, a diketopiperazine was introduced. A thiophenyl group served as a precursor of the isopropylidene function. Implementation of the same sort of chemistry starting with a methoxytryptophan derivative led to the parent structures. Furthermore, it was shown that the difficultly accessible isopropylidene side chain of spirotryprostatin A is not necessary for biological activity. Moreover, three analogues lacking the diketopiperazine system were shown to be quite active as cell cycle inhibitors.

The total synthesis of spirotryprostatin A

Eight concise steps suffice for the first total synthesis of the title compound 1, which inhibits the transitions from the G2 and M phases into the next phases of the cell cycle. Key steps in the synthesis are a stereocontrolled oxidative rearrangement of