Phosphate → 21-Deoxyconcanolide A

HRID 976030Notes

Reaction equation

HRID 976030 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][CH2:13][C@@H:14]1[C@H:32]([OH:33])[C@H:31]([CH3:34])[CH:30]=[C:29]([CH3:35])[CH:28]=[C:27]([O:36][CH3:37])[C:25](=[O:26])[O:24][C@H:23]([C@H:38]([C@@H:40]([OH:66])[C@@H:41]([C@@H:43]2[O:48][C@H:47](/[CH:49]=[CH:50]/[CH3:51])[C@@H:46]([CH3:52])[C@H:45]([O:53][C@@H]3O[C@H](C)[C@@H](OC(N)=O)[C@H](O)C3)[CH2:44]2)[CH3:42])[CH3:39])[C@@H:22]([O:67][CH3:68])[CH:21]=[CH:20][CH:19]=[C:18]([CH3:69])[CH2:17][C@@H:16]([CH3:70])[C@@H:15]1[OH:71].P([O-])([O-])([O-])=O>Cl.CO>[CH3:12][CH2:13][C@@H:14]1[C@H:32]([OH:33])[C@H:31]([CH3:34])[CH:30]=[C:29]([CH3:35])[CH:28]=[C:27]([O:36][CH3:37])[C:25](=[O:26])[O:24][C@H:23]([C@H:38]([C@@H:40]([OH:66])[C@@H:41]([C@@H:43]2[O:48][C@H:47](/[CH:49]=[CH:50]/[CH3:51])[C@@H:46]([CH3:52])[C@H:45]([OH:53])[CH2:44]2)[CH3:42])[CH3:39])[C@@H:22]([O:67][CH3:68])[CH:21]=[CH:20][CH:19]=[C:18]([CH3:69])[CH2:17][C@@H:16]([CH3:70])[C@@H:15]1[OH:71]

Participants

6

Reactant 3

HCID 1061PhosphateHCID 6101p-Toluenesulfonic acidHCID 1111555021-deoxyconcanamycin A

Product 1

HCID 1107245421-Deoxyconcanolide A

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

500 mg (2.6 mmol, 22.5 equiv.) of toluene-4-sulfonic acid in 3 ml of 1N HCl are added to a solution of 100 mg of 21-deoxyconcanamycin A (0.117 mmol) in 15 ml of MeOH and the reaction mixture is stirred for 48 hours at room temperature. After the addition of 20 ml of phosphate buffer (pH=7) the solvent is removed in vacuo. Standard working-up, followed by column chromatography on silica gel (system E then system D), yields the title compound. M.p. 104° C.

Workup

  1. customis removed in vacuo

Sources & evidence

ORD record
ord-bb1100e89c704bda929497575780005a
Source dataset
uspto-grants-1997_03
Patent number
US05610178

Reaction notes

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