Total Synthesis of the Eight Diastereomers of the Syn-Anti-Syn Phytoprostanes F1 Types I and II
Authors:
- 5 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (7) , 2498-2503
Abstract
Syntheses of the eight enantiomerically pure diastereomers of the syn-anti-syn phytoprostanes F1 types I and II are described starting from d- and l-glucose. Key steps include Wittig coupling, Horner Wadsworth Emmons (HWE) reactions, and enantioselective reduction of α,β-unsaturated ketones.Keywords
This publication has 12 references indexed in Scilit:
- Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plantsThe Plant Journal, 2003
- Total synthesis of phytoprostane F1 and its 16 epimerTetrahedron Letters, 2003
- Isoprostanes as a biomarker of lipid peroxidation in humans: physiology, pharmacology and clinical implicationsTrends in Pharmacological Sciences, 2002
- Plant defense in the absence of jasmonic acid: The role of cyclopentenonesProceedings of the National Academy of Sciences, 2001
- Analysis of Oxidative Stress and Wound-Inducible Dinor Isoprostanes F1 (Phytoprostanes F1) in PlantsPlant Physiology, 2000
- Formation of isoprostane F2-like compounds (phytoprostanes F1) from α-linolenic acid in plantsFree Radical Biology and Medicine, 2000
- Measurement of F2-isoprostanes as an index of oxidative stress in vivoFree Radical Biology and Medicine, 2000
- F4 ‐ Isoprostanes as Specific Marker of Docosahexaenoic Acid Peroxidation in Alzheimer's DiseaseJournal of Neurochemistry, 1999
- F4-Isoprostanes: A Novel Class of Prostanoids Formed during Peroxidation of Docosahexaenoic Acid (DHA)Biochemical and Biophysical Research Communications, 1998
- A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism.Proceedings of the National Academy of Sciences, 1990