Cephalotaxine → HCID 56841046, compound

HRID 1175700Notes

Reaction equation

[CH3:1][C:2]([OH:39])([CH2:4][CH2:5][CH2:6][C@:7]([OH:38])([C:13]([O:15][C@@H:16]1[C:32]([O:33][CH3:34])=[CH:31][C@:27]23[CH2:28][CH2:29][CH2:30][N:26]2[CH2:25][CH2:24][C:23]2[CH:22]=[C:21]4[O:35][CH2:36][O:37][C:20]4=[CH:19][C:18]=2[C@H:17]13)=[O:14])[CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH3:3].COC1[C@@H](O)[C@@H]2[C@@]3(N(CCC4C=C5OCOC5=CC=42)CCC3)C=1>>[CH3:3][C:2]([OH:39])([CH2:4][CH2:5][CH2:6][C@:7]([OH:38])([C:13]([O:15][C@@H:16]1[C:32]([O:33][CH3:34])=[CH:31][C@:27]23[CH2:28][CH2:29][CH2:30][N:26]2[CH2:25][CH2:24][C:23]2[CH:22]=[C:21]4[O:35][CH2:36][O:37][C:20]4=[CH:19][C:18]=2[C@H:17]13)=[O:14])[CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH3:1].[CH3:3][C:2]([OH:39])([CH2:4][CH2:5][CH2:6][C@@:7]([OH:38])([C:13]([O:15][C@@H:16]1[C:32]([O:33][CH3:34])=[CH:31][C@:27]23[CH2:28][CH2:29][CH2:30][N:26]2[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][C:20]4[O:37][CH2:36][O:35][C:21]=4[CH:22]=2)[C@H:17]13)=[O:14])[CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH3:1]

Participants

Reactant 2

HCID 65305Cephalotaxine

HCID 285033Omacetaxine Mepesuccinate

Product 2

HCID 285033Omacetaxine Mepesuccinate

HCID 56841046HCID 56841046, compoundYield 0.05%

Procedure

Crude homoharringtonine, prepared according to Example 25 from a partially racemized natural cephalotaxine and purified by chromatography and crystallisation according to the method A of Example 27, gave an homoharringtonine showing a non natural enantiomeric epi-homoharringtonine content less than 0.05%.

Workup

custompurified by chromatography and crystallisation

Sources & evidence

ORD record: ord-0a728b703d974aec9950c9cd6a6faa19
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842687B2

Reaction notes

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