The present application provides novel tetrahydro-isohumulone (THIAA) derivatives and substantially enantiomerically pure compositions and pharmaceutical formulations thereof. The application further provides methods of using the disclosed compounds and compositions to activate PPARγ, inhibit inflammation, and treat conditions associated with inflammation and conditions responsive to PPARγ modulation such as diabetes.

The present application provides novel tetrahydro-isohumulone (THIAA) derivatives and substantially enantiomerically pure compositions and pharmaceutical formulations thereof. The application further provides methods of using the disclosed compounds and compositions to activate PPARγ, inhibit inflammation, and treat conditions associated with inflammation and conditions responsive to PPARγ modulation such as diabetes.

The invention relates to processes for preparing carbaprostacyclin analogues and intermediates prepared from the processes. The invention also relates to cyclopentenone intermediates in racemic or optically active form.

The invention relates to processes for preparing carbaprostacyclin analogues and intermediates prepared from the processes. The invention also relates to cyclopentenone intermediates in racemic or optically active form.

This invention relates generally to the synthesis of Δ.sup.12-Prostaglandin J product using stereoretentive ruthenium olefin metathesis catalysts supported by dithiolate ligands. Δ.sup.12-Prostaglandin J products were generated with excellent selectivity (>99% Z) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield).

This invention relates generally to the synthesis of Δ.sup.12-Prostaglandin J product using stereoretentive ruthenium olefin metathesis catalysts supported by dithiolate ligands. Δ.sup.12-Prostaglandin J products were generated with excellent selectivity (>99% Z) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield).

[Problem] The present invention provides an industrially-preferable, cost-efficient, low-cost production method for 4-hydroxy-2-hydroxymethyl-2-cyclopenten-1-one (a compound represented by formula (I)) useful as a medicine, an agricultural chemical, or a raw material or intermediate of a medicine, an agricultural chemical, or the like. [Solution] According to the present invention, this compound represented by formula (I) is produced by subjecting an easily available compound represented by formula (II) (tri-O-acetyl-D-glucal) to a heating reaction in pressurized water.

[Problem] The present invention provides an industrially-preferable, cost-efficient, low-cost production method for 4-hydroxy-2-hydroxymethyl-2-cyclopenten-1-one (a compound represented by formula (I)) useful as a medicine, an agricultural chemical, or a raw material or intermediate of a medicine, an agricultural chemical, or the like. [Solution] According to the present invention, this compound represented by formula (I) is produced by subjecting an easily available compound represented by formula (II) (tri-O-acetyl-D-glucal) to a heating reaction in pressurized water.

[Problem]

The present invention provides an industrially-preferable, cost-efficient, low-cost production method for 4-hydroxy-2-hydroxymethyl-2-cyclopenten-1-one (a compound represented by formula (I)) useful as a medicine, an agricultural chemical, or a raw material or intermediate of a medicine, an agricultural chemical, or the like.

[Solution]

According to the present invention, this compound represented by formula (I) is produced by subjecting an easily available compound represented by formula (II) (tri-O-acetyl-D-glucal) to a heating reaction in pressurized water.

[Problem]

The present invention provides an industrially-preferable, cost-efficient, low-cost production method for 4-hydroxy-2-hydroxymethyl-2-cyclopenten-1-one (a compound represented by formula (I)) useful as a medicine, an agricultural chemical, or a raw material or intermediate of a medicine, an agricultural chemical, or the like.

[Solution]

According to the present invention, this compound represented by formula (I) is produced by subjecting an easily available compound represented by formula (II) (tri-O-acetyl-D-glucal) to a heating reaction in pressurized water.