Acetone → 8-Ethyl-1,6,7,8,10-pentahydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione

HRID 330584Notes

Reaction equation

HRID 330584 reaction equation
CC(C)=O.C(Cl)(Cl)Cl.[CH3:9][CH2:10][C@:11]1([OH:65])[C@H:20]([OH:21])[C:19]2[C:14](=[C:15](O)[C:16]3[C:31](=[O:32])[C:30]4[C:25](=[C:26](O)[CH:27]=[CH:28][C:29]=4[OH:33])[C:23](=[O:24])[C:17]=3[C:18]=2[OH:22])[C@@H:13]([O:36][C@@H]2O[C@@H](C)[C@@H](O[C@@H]3O[C@@H](C)[C@@H](O[C@@H]4O[C@@H](C)C(=O)CC4)[C@@H](O)C3)[C@@H](N(C)C)C2)[CH2:12]1>CO>[CH3:9][CH2:10][C@:11]1([OH:65])[C@H:20]([OH:21])[C:19]2[C:18]([OH:22])=[C:17]3[C:23](=[O:24])[C:25]4[CH:26]=[CH:27][CH:28]=[C:29]([OH:33])[C:30]=4[C:31](=[O:32])[C:16]3=[CH:15][C:14]=2[C@@H:13]([OH:36])[CH2:12]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 6212ChloroformHCID 157444beta-Isorhodomycinone

Product 1

HCID 1676958-Ethyl-1,6,7,8,10-pentahydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The resulting broth (about 12 liters) was similarly subjected to acid hydrolysis, acetone extraction from the mycelia and chloroform extraction, and finally 9.8 g of a crude powder containing β-isorhodomycinone. The whole amount of the crude powder was dissolved in 100 ml of methanol and the insoluble materials were centrifuged off. After concentration, the soluble fraction was applied on a silica-gel column (diameter: 78 mm) packed with 300 g of the above-mentioned silica-gel C-200 in chloroform, and eluted with 500 ml of chloroform, 100 ml of a mixture solution of chloroform/methanol (500/1), 3400 ml of the mixture solution (400/1) and 1000 ml of the mixture solution (300/1) in this order. β-isorhodomycinone was eluted with a mixture of chloroform/methanol (400/1). The β-isorhodomycinone-containing fractions were collected and evaporated to dryness followed by washing with ether The yield of β-isorhodomycinone was 0.62 g. The identification of this compound was carried out by means of 1H--M=NMR and 13C--NMR spectra and UV and FD mass spectra thereof, referring chemical data described in the literature (Chem. Ber., Vol. 98, page 3145, 1965).

Workup

  1. concentrationAfter concentration
  2. washeluted with 500 ml of chloroform, 100 ml of a mixture solution of chloroform/methanol (500/1), 3400 ml of the mixture solution (400/1) and 1000 ml of the mixture solution (300/1) in this order
  3. washβ-isorhodomycinone was eluted with a mixture of chloroform/methanol (400/1)
  4. additionThe β-isorhodomycinone-containing fractions
  5. customwere collected
  6. customevaporated to dryness
  7. washby washing with ether The yield of β-isorhodomycinone

Sources & evidence

ORD record
ord-abdf2890915d4e8c994cd4ddae2f2f40
Source dataset
uspto-grants-1990_01
Patent number
US04897470

Reaction notes

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