ChemicalBook CAS DataBase List Lurbinectedin

Lurbinectedin synthesis

6synthesis methods

Product Name:Lurbinectedin
CAS Number:497871-47-3
Molecular formula:C41H44N4O10S
Molecular Weight:784.88

Phenol 268 was subjected to oxidative dearomatization using phenylselenic anhydride. Subsequent esterification of the primary alcohol with (R)-N-Alloc-S-Fm-Cys (269) gave the hydroxy enone 270 in 72% overall yield for this two-step reaction. Macrocyclization followed the one-pot protocol reported by Corey to afford the sulfide 271 in 51% yield. Reduction to remove all allyl and Alloc protecting groups afforded the amine 272 in 85% yield. Amine 272 was reacted with 4-carboxaldehyde-1-methylpyridinium salt (273) to afford the oxalate 274 in 52% yield. Pictet-Spengler reaction with the tryptophan derivative 275 followed by iminium ion-mediated quenching of the cyano group by injection and hydrolysis afforded rubicin in 77% overall yield.
Lurbinectedin synthesis

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Yield:-

Steps:

Multi-step reaction with 16 steps
1.1: water; lithium hydroxide / tetrahydrofuran
2.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide / 2 h / 23 °C
2.2: 3 h / 23 °C
3.1: trifluoroacetic acid / dichloromethane / 1.5 h / 23 °C
4.1: dichloromethane / 2 h / 23 °C
5.1: chloro-trimethyl-silane; methanol / 1.5 h / 23 °C
6.1: water; disodium hydrogenphosphate; sodium nitrite; phosphoric acid / dichloromethane / 19 h / 23 °C
7.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 23 °C
8.1: dmap; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 23 °C
9.1: tri-n-butyl-tin hydride; acetic acid / bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.75 h / 23 °C
10.1: hydrogen / palladium 10% on activated carbon / acetonitrile / 2.5 h / 23 °C
10.2: 20 h / 23 - 70 °C
11.1: benzeneseleninic anhydride / dichloromethane
12.1: trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide; tert-butyl alcohol
13.1: methanesulfonic acid / dichloromethane
14.1: oxalic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-methylpyridine-4-carboxaldehyde iodide
15.1: acetic acid
16.1: water; silver nitrate / acetonitrile

References:

WO2011/147828,2011,A1

Spiro[6,16-(epithiopropanoxymethano)-7,13-imino-12H-1,3-dioxolo[7,8]isoquino[3,2-b][3]benzazocine-20,1'-[1H]pyrido[3,4-b]indole]-14-carbonitrile, 5-(acetyloxy)-2',3',4',6,6a,7,9',13,14,16-decahydro-8-hydroxy-6',9-dimethoxy-4,10,23-trimethyl-19-oxo-, (1'R,6R,6aR,7R,13S,14R,16R)- (9CI)

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References

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References

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References

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References

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