Donald B. Miller

Stereocontrol of Michael hydride reduction by a remote hydroxyl group. A strategy for stereorational total synthesis of spatane diterpenes

Synthese du spatadiene-13,17 ol-5 a partir de la cyclopentene-2one et de la methyl-6 norbornene-5 one-2

Total synthesis of anhydro levug̀landin D2

Abstract Total synthesis of anhydro levuglandin D 2 [9-acetyl-8-formyl-5(Z),9(E),11(E)-hepta-decatrienoic acid] confirms the structure assigned to this 9,10-seco prostanoic acid product from solvent induced rearrangement of the prostaglandin endoperoxide PGH 2 in aqueous solution.

Effects of E2 levuglandins on the contractile activity of the rat uterus

The effects of E2 levuglandins on the contractile activity of rat uterine horns were studied. LGE2, AnLGE2, delta 9-LGE2 and the synthetic epimer, 8-epi-delta 9-LGE2 all induced contractions in a dose-response fashion. AnLGE2 gave decreased responses with increased bath concentrations. Paired comparisons showed potent and selective inhibitory effects of AnLGE2 on the uterotonic activity of prostaglandins. AnLGE2 inhibited the uterotonic activity of PGE2 at a 0.1:1 ratio, of PGD2 at a 1:1 ratio, but did not inhibit the activity of PGF2 alpha. Exposure of spontaneously contracting uteri to high concentrations of AnLGE2, or prolonged exposure to lower concentrations, suppressed contractions.

Anhydrolevuglandin D2 inhibits the uterotonic acivity of prostaglandins F2α and D2

Abstract Anhydrolevuglandin D 2 (AnLGD 2 ), which is produced from PGH 2 by a water-induced rearrangement and subsequenct dehydration, is uterotonic. However, increasing concentrations caused decreased responses of the uterine horns. AnLGD 2 inhibited responses of uteri to stimulation by specific prostaglandins. PGF 2α was inhibited at an AnLGD 2 :PGF 2α ratio of 0.05:1 with 5 to 25 pg/ml concentrations of PGF 2α . The response to PGD 2 was inhibited at an AnLGD 2 :PGD 2 ratio of 0.05:1 with PGD 2 concentrations of 5 to 75 pg/ml. In contrast, the uterotonic effects of PGE 2 werer not inhibited by AnLGD 2 . When AnLGD 2 was added to baths with contracting uteri it inhibited contractions less if the exposure period was 5 min than if it was 10 min. The longer exposure times produced prolonged inhibition of contractile activity with bath concentrations of AnLGD 2 as little as 2.5 pg/ml.