35804-91-2

Usage

Uses

Used in Pharmaceutical Research:
JBIR-94 is utilized as a compound in pharmaceutical research, specifically for exploring its potential interactions with biological receptors and its efficacy as a therapeutic agent. (4aR,7S)-4-Acetyl-6α,9α-epimino-4aβ,5,6,8,9,9aβ-hexahydro-1'-methylspiro[cyclohepta[c]pyran-7(1H),3'-[3H]indol]-2'(1'H)-one's unique structure and properties make it a promising candidate for drug discovery, although more research is required to determine its full potential and applications in medicine.
Used in Drug Discovery:
In the field of drug discovery, JBIR-94 serves as a valuable compound for investigating its possible pharmacological activities. Its complex structure and molecular composition contribute to its potential as a therapeutic agent, making it a subject of interest for further study and development.

Upstream product

• 219583-98-9 (6S,10S)-5-methyl-8-(1'-ethyl-2'-propenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctaindole-9-carboxaldehyde 
• 219584-09-5 C₂₇H₃₀N₂O 
• 478910-95-1 C₂₈H₃₂N₂O₄ 
• 197143-13-8 (6S,10S)-(-)-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cycloocta[b]indole 
• 84094-74-6 (1S,3R)-(-)-methyl 2-benzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 201221-35-4 C₂₁H₂₀N₂O₂ 
• 277752-62-2 C₂₈H₃₄N₂O₃ 

Relevant academic research and scientific papers

Concise Total Synthesis of (?)-Affinisine Oxindole, (+)-Isoalstonisine, (+)-Alstofoline, (?)-Macrogentine, (+)-Na-Demethylalstonisine, (?)-Alstonoxine A, and (+)-Alstonisine

A highly enantio- and diastereoselective strategy to access any member of the sarpagine/macroline family of oxindole alkaloids via internal asymmetric induction was developed from readily available d-(+)-tryptophan. At the center of this approach was the diastereospecific generation of the spiro[pyrrolidine-3,3′-oxindole] moiety at an early stage via a tert-butyl hypochlorite-promoted oxidative rearrangement of a chiral tetrahydro-β-carboline derivative. This key branching point determined the spatial configuration at the C-7 spiro center to be entirely 7R or 7S. Other key stereospecific processes were the asymmetric Pictet–Spengler reaction and Dieckmann cyclization, which were scalable to the 600 and 150 gram levels, respectively. Execution of this approach resulted in first enantiospecific total synthesis of (+)-isoalstonisine and (?)-macrogentine from the chitosenine series (7R), as well as (+)-alstonisine, (+)-alstofoline, (?)-alstonoxine A and (+)-Na-demethylalstonisine from the alstonisine series (7S).

Enantiospecific synthesis of (+)-alstonisine via a stereospecific osmylation process

The first enantiospecific total synthesis of (+)-alstonisine has been accomplished from D-tryptophan methyl ester 13 in 12% overall yield (in 17 reaction vessels). A diastereospecific osmylation process has been employed as a key step to convert indole 18 into spirocyclic oxindole 19. Mechanistic studies of the stereoselective osmylation of the 2,3-indole double bond of indole alkaloids has been carried out. Compelling evidence for the intramolecular delivery of OsO4 via Nb-complexation was obtained for the osmylation process. The correct structure of (+)-alstonisine (1) was determined by NOE spectroscopic experiments and further confirmed by single-crystal X-ray analysis.

Enantiospecific, stereospecific total synthesis of the oxindole alkaloid alstonisine

(equation presented) The total synthesis of alstonisine was accomplished in enantiospecific fashion in an overall yield of 12% (from tryptophan methyl ester) in 17 reaction vessels. The structure of alstonisine (1) has been determined by NOE spectroscopic