11-deoxy-prostaglandin

The Michael addition of (+)-(5 )-51 to the aj3-unsaturated ketone 217 constitutes a key step in the asymmetric synthesis of the optically active cyclopentanone 318, which is precursor of the 11-deoxy-prostaglandins (321). 

Advantage was taken of the Wharton reaction to carry out an oxygen transposition of 32 to provide 33, which was only two steps away from 11-deoxy-prostaglandin Fi0 after de-silylation and hydrolysis.18... 

Natural PPARy Ligands. Endogenous ligands demonstrated to bind and activate PPARy in vitro include unsaturated fatty acids and their derivatives such as prostaglandin J2 (15-deoxy-A12,l4-PGJ2). Consistent... 

Lin, C.-H., Aristoff, P.A., Johnson, P.D., McGrath, J.P., Timko, J.M., and Robert, A., Benzidine prostaglandins synthesis of optically pure 15-deoxy-U-68,215 and its enantiomer via a modified intramolecular Wadsworth-Emmons-Wittig reaction, /. Org. Chem., 52, 5594, 1987. 

In a similar manner, Brummond et al. demonstrated the first total synthesis of 15-deoxy-A12,14-prostaglandin J2 (162) that was completed using a silicon-tethered allenic Pauson-Khand reaction to obtain the highly unsaturated cyclopentenone substructure [36]. Treatment of alkynylallene 160 with molybdenum hexacarbonyl and dimethyl sulfoxide affords the desired cycloadduct 161 in 43% yield (Scheme 19.30). Trienone 161 was obtained as a 2 1 Z E mixture of isomers in which the Z-isomer could be isomerized to the desired E-isomer. The silicon tether was cleaved and the resulting product converted to 15-deoxy-A12,14-prostaglandin J2 (162). 

Peroxisome proliferator-activted receptor, PPAR 15-Deoxy-A12,14-prostaglandin J2 AGGTCA DR-1... 

Maxey KM Eicosanoids acting via nuclear receptors The 15-deoxy PGJ compounds and congeners. Prostaglandins Other Lipid Mediat 2000 62 1. 

Maggi, L. B.Jr., Sadeghi, H., Weigand, C., Scarim, A. L., Heitmeier, M. R., and Corbett, J. A. (2000). Anti-inflammatory actions of 15-deoxy-delta 12,14-prostaglandin J2 and troglitazone Evidence for heat shock-dependent and -independent inhibition of cytokine-induced inducible nitric oxide synthase expression. Diabetes 49, 346-355. 

The predecessor of Ultraflne was the Fine Chemicals Unit of Salford University Industrial Centre, which was set up partly to exploit a new route to prostaglandins.9 When the independent company was founded, it made sense to offer other eicosanoids. A key intermediate for the synthesis of leukotriene A4 (LTA4) (7), and thence LTC4, LTD4, and LTE4, was the epoxyalcohol (10), whose synthesis from 2-deoxy-D-ribose (8) (Scheme 29.2) had been reported.10... 

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