87248-11-1

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 
• 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 
• 870-63-3 prenyl bromide 
• 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 

Relevant academic research and scientific papers

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