71239-65-1

Usage

Uses

Used in Pharmaceutical Industry:
Flustramine B is used as a pharmaceutical compound for its potential therapeutic applications. As an alkaloid, it may possess bioactive properties that can be harnessed for the development of new drugs or treatments.
Used in Chemical Research:
Flustramine B is used as a research compound in the field of chemistry, particularly in the study of stereoisomerism and the exploration of novel chemical structures derived from marine sources.
Used in Marine Biology:
Flustramine B is used as a subject of study in marine biology, contributing to the understanding of the chemical diversity and ecological roles of marine organisms, such as Bryozoan Flustrafoleacea.

InChI:InChI=1/C21H29BrN2/c1-15(2)8-10-21-11-13-23(5)20(21)24(12-9-16(3)4)19-14-17(22)6-7-18(19)21/h6-9,14,20H,10-13H2,1-5H3/t20-,21+/m0/s1

Upstream product

• 105708-75-6 6-bromo-1-methyl-3a,8-bis(3-methyl-2-buten-1-yl)-2-oxo-2,3,3a,8a-tetrahydro-8H-furo[2,3-b]indole 
• 870-63-3 prenyl bromide 
• 87202-06-0 6-Bromo-3a,8-bis-(3-methyl-but-2-enyl)-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester 
• 88369-04-4 8-acetyl-1-methoxycarbonyl-5-nitro-1,2,3,3a,8a-hexahydropyrrolo<2,3-b>indole 
• 87202-05-9 8-Acetyl-6-bromo-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1-carboxylic acid methyl ester 
• 87202-02-6 methyl (2-(6-bromo-1H-indol-3-yl)ethyl)carbamate 
• 87202-08-2 6-Bromo-3a,8-bis-(3-methyl-but-2-enyl)-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole 
• 74-88-4 methyl iodide 
• 1040732-54-4 1-Acetyl-2,6-dibromo-1,2-dihydro-indol-3-one 
• 114165-31-0 1-acetyl-6-bromoindolin-3-one 
• 877797-41-6 C₂₀H₂₃BrN₂O 
• 877797-40-5 C₁₅H₁₅BrN₂O 
• 877797-39-2 2-{(S)-6-bromo-3-[(E)-non-2-enyl]-2-oxoindolin-3-yl}acetonitrile 
• 877797-38-1 C₁₉H₂₄BrNO₃ 

Relevant academic research and scientific papers

Development of the Regiodivergent Asymmetric Prenylation of 3-Substituted Oxindoles

This paper describes our efforts to design a Pd-catalyzed asymmetric prenylation of 3-substituted oxindoles that affords access to both the linear and reverse-prenylated products. Both 3-alkyl- and 3-aryloxindoles performed well under our optimized reaction conditions. The regiodivergent alkylation of monoterpene-derived electrophiles using this methodology was also investigated. The utility of this methodology in natural product synthesis was demonstrated through the efficient total syntheses of four Flustra alkaloids, which also allowed the absolute stereochemistry of the prenylated oxindole products to be assigned. Surprisingly, the same enantiomer of ligand produced linear and branched regioisomers of opposite chirality.

Exercising regiocontrol in palladium-catalyzed asymmetric prenylations and geranylation: Unifying strategy toward flustramines A and B

Pd-catalyzed asymmetric prenylation of oxindoles to afford selectively either the prenyl or reverse-prenyl product has been demonstrated. Control of the regioselectivity in this transformation is governed by the choice of ligand, solvent, and halide additive. The resulting prenylated and reverse-prenylated products were transformed into ent-flustramides and ent-flustramines A and B. Additionally, control of the regio-and diastereoselectivity was obtained using π-geranylpalladium complexes.

Total synthesis of (-)-flustramine B via one-pot intramolecular ullmann coupling and claisen rearrangement

Total synthesis of (-)-flustramine B was achieved via one-pot intramolecular Ullmann coupling and Claisen rearrangement. A striking feature of this method of synthesis is that the sequential intramolecular Ullmann coupling and Claisen rearrangement reactions proceeds with concomitant deprotection of the methoxymethyl (MOM) group to afford spirocyclic oxindole with perfect asymmetric transmission in good overall yield.

Enantioselective total synthesis of (-)-flustramines A, B and (-)-flustramides A, B via domino olefination/isomerization/Claisen rearrangement sequence

The concise total synthesis of marine alkaloids, (-)-flustramines A and B, and (-)-flustramides A and B has been achieved through the domino olefination/isomerization/Claisen rearrangement (OIC) for highly enantioselective construction of the asymmetric quaternary carbon center and the chemoselective reduction-cyclization (RC) for pyrrolidine formation as key steps. The Royal Society of Chemistry 2006.

Total syntheses of five indole alkaloids from the marine bryozoan Flustra foliacea

A general, efficient, and conceptually new approach to the total syntheses of marine-derived indole alkaloids, including (±)-flustramines A (1) and B (2), (±)-flustramides A (3) and B (4), and (±)-debromoflustramine B (5), is outlined. The key step in the syntheses involves the conjugated addition of an organomagnesium species derived from prenyl bromide to 2-hydroxyindolenines. Compounds 1, 2, and 5 have been synthesized in five steps with 23%, 17%, and 16% overall yield, respectively, whereas flustramides 3 and 4 have been synthesized in only four steps with 24% and 18% overall yield, respectively, on the basis of 2-hydroxyindolenines.

SYNTHESIS OF (+/-)-FLUSTRAMINE B, A MARINE ALKALOID

6-Bromo-Nb-methoxycarbonyltryptamine (7) was prepared from 5-nitropyrroloindole (4a) by a series of reactions: reduction, bromination, deamination, and ring opening.Prenylation of 7 with an excess dimethylallyl bromide gave the 3a,8-diprenylpyrroloindole (8).Hydrolysis of 8 followed by methylation with MeI-K2CO3-acetone provided (+/-)-flustramine B.KEYWORDS --- flustramine B; bromination; prenylation; cyclic tautomer; tryptamine; 6-bromotryptamine; pyrroloindole