Regio- and Stereoselective Reactions of 17-Phenyl-18,19,20-trinorprostaglandin F2α Isopropyl Ester
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (12) , 4028-4034
- https://doi.org/10.1021/jo960098t
Abstract
Novel prostaglandin F(2)(alpha) derivatives, functionalized at C13 and C14, have been prepared. 17-Phenyl-18,19,20-trinorprostaglandin F(2)(alpha) isopropyl ester [(15S)-1] and its epimer [(15R)-1] were stereoselectively epoxidized, using Sharpless conditions, to produce each of the four diastereomeric epoxides (15S)-2, (15S)-3, (15R)-2, and (15R)-3. Treatment of the four epoxides with LiOH stereospecifically-produced the pentahydroxy substituted analogues 12 and 13. Alternatively, epoxides 2 and 3were allowed to react with thiophenolate ion. The attack of the sulfur nucleophile on the epoxide occurred at either C13 or C14 depending on the stereochemistry of the epoxide and of C15.Keywords
This publication has 13 references indexed in Scilit:
- Derivatives of 17-Phenyl-18,19,20-trinorprostaglandin F2.alpha. Isopropyl Ester: Potential Antiglaucoma AgentsJournal of Medicinal Chemistry, 1995
- Palladium catalyzed syntheses of phenyl-substittuted pgf2α analogues: potential antigluaucoma agentsBioorganic & Medicinal Chemistry Letters, 1993
- Phenyl substituted prostaglandin analogs for glaucoma treatmentDrugs of the Future, 1992
- The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspectsChemical Reviews, 1989
- Mechanism of the gas-phase thermolysis of monomethylsilaneJournal of the American Chemical Society, 1987
- On the Mechanism of Asymmetric Epoxidation with Titanium—Tartrate CatalystsPublished by Elsevier ,1985
- Horner-wadsworth-emmons reaction: Use of lithium chloride and an amine for base-sensitive compoundsTetrahedron Letters, 1984
- The first practical method for asymmetric epoxidationJournal of the American Chemical Society, 1980
- Prostaglandin D2 as a potential antithrombotic agentProstaglandins, 1975
- Synthesis of vinyl halides and vinyl silanes via alkaline decomposition of 5,5-dialkyl-3-nitrosooxazolidinonesJournal of the American Chemical Society, 1969