Eudistomin O → Brovincamine

HRID 330106Notes

Reaction equation

HRID 330106 reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[NH:12]2)=[CH:4][CH:3]=1.BrC1C=C2[C:19]([C:20]3[CH2:21][CH2:22]N[C:24](C)([C:29]([O:31][CH3:32])=[O:30])[C:25]=3N2)=[CH:18][CH:17]=1.BrC1C=C2C(C3CCNC(C)(C(OCC)=[O:49])C=3N2)=CC=1.BrC1C=C2C(C3CCNC(C(OCC)=O)C=3N2)=CC=1.BrC1C=C2C(C3CCNC(C(OCC4C=CC=CC=4)=O)C=3N2)=CC=1>>[CH3:22][CH2:21][C@:20]12[CH2:25][C@:24]([OH:49])([C:29]([O:31][CH3:32])=[O:30])[N:12]3[C:11]4=[C:6]([C:5]5[CH:4]=[CH:3][C:2]([Br:1])=[CH:14][C:13]=53)[CH2:7][CH2:8][N:9]([C@@H:10]14)[CH2:17][CH2:18][CH2:19]2

Participants

5

Reactant 4

HCID 145928Eudistomin OHCID 19870750HCID 19870750, compoundHCID 19870753HCID 19870753, compoundHCID 70373879HCID 70373879, compound

Product 1

HCID 68771Brovincamine

Procedure

The method as claimed in claim 1, wherein the 7-bromo-β-carboline compound of the formula (I) is selected from the group consisting of 7-bromo-1-methyl-1-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline-7-bromo-1-methyl-1-ethoxycarbonyl-1,2,3,4-tetrahydro-β-carboline, 7-bromo-1-ethoxycarbonyl-1,2,3,4-tetrahydro-β-carboline and 7-bromo-1-benzyloxycarbonyl-1,2,3,4-tetrahydro-β-carboline.

Sources & evidence

ORD record
ord-613681efeb6042e9a908580c0ea5382b
Source dataset
uspto-grants-1990_01
Patent number
US04894457

Reaction notes

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