Prostaglandin FM → 13,14-Dihydro-15-keto-PGD2

HRID 1461013Notes

Reaction equation

[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH2:8][CH2:9][C@@H:10]1[C@@H:14]([CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C@@H:13]([OH:24])[CH2:12][C@H:11]1[OH:25])=[O:7].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH2:8][CH2:9][C@H:10]1[C:11](=[O:25])[CH2:12][C@H:13]([OH:24])[C@@H:14]1[CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:7]

Participants

Reactant 2

HCID 5283039Prostaglandin FM

HCID 131709961Jones' reagent

Product 1

HCID 528303613,14-Dihydro-15-keto-PGD2

Procedure

Carboxylic acid (8) was deketalized according to the usual method to give 13,14-dihydro-15-keto-PGF2 α (10). The resultant (10) was oxidized with Jones reagent to give 13,14-dihydro-15-keto-PGD2 (11), R=H.

Sources & evidence

ORD record: ord-61c255c8dae548b784d0ea0ffdfdf1be
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05073569

Reaction notes

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