17-Ethyl-1,14-dihydroxy-12-[1-(4-hydroxy-3-methoxycyclohexyl)prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone → 1,2,14-Trihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-17-ethyl-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-3,10,16-trione

HRID 1646164Notes

Reaction equation

HRID 1646164 reaction equation
[OH:1][C:2]12[O:32][CH:25]([CH:26]([O:30][CH3:31])[CH2:27][CH:28]1[CH3:29])[CH:24]([O:33][CH3:34])[CH2:23][CH:22]([CH3:35])[CH2:21][C:20]([CH3:36])=[CH:19][CH:18]([CH2:37][CH3:38])[C:17](=[O:39])[CH2:16][CH:15]([OH:40])[CH:14]([CH3:41])[CH:13]([C:42]([CH3:53])=[CH:43][CH:44]1[CH2:49][CH2:48][CH:47]([OH:50])[CH:46]([O:51][CH3:52])[CH2:45]1)[O:12][C:11](=[O:54])[CH:10]1[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]1)[C:4](=[O:55])[C:3]2=[O:56].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[OH:1][C:2]12[O:32][CH:25]([CH:26]([O:30][CH3:31])[CH2:27][CH:28]1[CH3:29])[CH:24]([O:33][CH3:34])[CH2:23][CH:22]([CH3:35])[CH2:21][C:20]([CH3:36])=[CH:19][CH:18]([CH2:37][CH3:38])[C:17](=[O:39])[CH2:16][CH:15]([OH:40])[CH:14]([CH3:41])[CH:13]([C:42]([CH3:53])=[CH:43][CH:44]1[CH2:49][CH2:48][CH:47]([OH:50])[CH:46]([O:51][CH3:52])[CH2:45]1)[O:12][C:11](=[O:54])[CH:10]1[N:5]([CH2:6][CH2:7][CH2:8][CH2:9]1)[C:4](=[O:55])[CH:3]2[OH:56]

Participants

4

Reactant 2

HCID 224117-Ethyl-1,14-dihydroxy-12-[1-(4-hydroxy-3-methoxycyclohexyl)prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetroneHCID 5948Tributylstannane

Product 1

HCID 773814381,2,14-Trihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-17-ethyl-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-3,10,16-trioneYield 62.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1,14-dihydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-17-ethyl-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo [22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (FR-900520, EP 184162) (80 mg) and tri-n butyltin hydride (0.2 ml) in toluene (5ml) was heated at 70° C. for 2 hours. The cooled reaction mixture was then evaporated in vacuo and the residue purified by column chromatogragphy on silica eluting with ethyl acetate to give the title compound as a foam (50 mg).

Workup

  1. customThe cooled reaction mixture
  2. customwas then evaporated in vacuo
  3. customthe residue purified by column chromatogragphy on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-a0ba8e5e9b254342a8231b4bfeea0b05
Source dataset
uspto-grants-1993_01
Patent number
US05179087

Reaction notes

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