Progress Toward the Total Synthesis of Ergot Alkaloids: PDF
Preview Progress Toward the Total Synthesis of Ergot Alkaloids:
Progress Toward the Total Synthesis of Ergot Alkaloids: Cody Timmons Wipf Group 12/23/2006 University of Pittsburgh Cody Timmons @ Wipf Group 1 1/1/2007 Ergot Alkaloids CO R CH 2 3 NMe NMe H H HN HN Lysergic acid subclass Clavine subclass Cody Timmons @ Wipf Group 2 1/1/2007 Ergot Alkaloids CO R CH 2 3 NMe NMe H H Common tetracyclic HN HN core Lysergic acid subclass Clavine subclass Cody Timmons @ Wipf Group 3 1/1/2007 Ergot Alkaloids CO R CH 2 3 NMe NMe H H Tryptophan subunit HN HN Lysergic acid subclass Clavine subclass Cody Timmons @ Wipf Group 4 1/1/2007 Lysergic Acid Compounds CO H CONEt 2 2 NMe NMe H H HN HN Lysergic acid Lysergic acid diethyl amide (LSD) Cody Timmons @ Wipf Group 5 1/1/2007 Clavine Compounds OH OH CH 3 H H H NHMe NMe NMe H H H HN HN HN Chanoclavine-I Agroclavine Elymoclavine Cody Timmons @ Wipf Group 6 1/1/2007 History Ergotism (aka St. Anthony’s Fire) Disease resulting from eating cereal grains (esp. rye) infected with ergot fungus Ergot on a head of grain Cody Timmons @ Wipf Group 7 1/1/2007 History Ergotism (aka St. Anthony’s Fire) Symptoms include: convulsions, vomiting, hallucinations, gangrene, insanity, and death Last epidemic: 2001-Ethiopia Cause of Salem Witch Trials? Cody Timmons @ Wipf Group 8 1/1/2007 Physiological Effects OH • Ergolines: bind serotonin NH 2 receptors…induce mood swings, vomiting, vasoconstriction, HN gangrene, convulsions Serotonin (5-hydroxytryptamine) X • Historical uses: abortive agent, controlling maternal bleeding, NMe hallucinogen, treatment of H Parkinson’s disease, migraine HN Ergoline Skeleton Cody Timmons @ Wipf Group 9 1/1/2007 Literature Highlights: Lysergic Acid Woodward, 1954, 1956: O O O O CO H NMe 2 1) SOCl2 1) Br2 1) HCl 2) NaOMe 2) AlCl3 2) BzN BzN O O BzN NHMe O Cl CO H 2 1) NaBH 1) NaCN / HCN 4 NMe NMe NMe 2) SOCl / SO 2) hydrolysis 2 2 3) Raney Ni HN HN HN JACS, 1954, 76, 5256. JACS, 1956, 78, 3087. Cody Timmons @ Wipf Group 10 1/1/2007
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