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pg试玩入口:Heterocyclic Chemistry Class

文字:[大][中][小] 手机页面二维码 2016/12/7     浏览次数:    

Professor Phil Baran
email: pbaran@scripps.edu 
website

TAs:
Julian Lo, BCC-439, 784-7372
email: julianlo@scripps.edu

Matthew Villaume , BCC-457, 784-7372
email: villaume@scripps.edu

Texts: 
Joule and Mills, "Heterocyclic Chemistry"
Ishihara, Montero, and Baran, "The Portable Chemist's Consultant: A Survival Guide for Discovery, Process, and Radiolabeling" 

Time: 8:00am - 9:30am (unless specified otherwise) 
Location: Keck Auditorium (BCC-1)

  • Syllabus
  • Essentials of Heterocyclic Chemistry I
  • Essentials of Heterocyclic Chemistry II
  • Essentials of Heterocyclic Chemistry III
  • Essentials of Heterocyclic Chemistry IV
  • Patrick Lam's Electrostatic Potential Maps

 

  • Lecture 1: Tuesday, March 31st - General Reactivity I
    • J. Org. Chem. 1994, 59, 3656-3664.
    • Eur. J. Org. Chem. 2002, 4095-4122.
  • Lecture 2: Wednesday, April 1st - General Reactivity II
    • Pyridinium Photochemistry (Richter, 2005)
    • Chemistry of 1-Acyl Pyridiniums (Lin, 2006)
    • J. Am. Chem. Soc. 2000, 122, 5017-5024.
    • J. Am. Chem. Soc. 1988, 110, 7445-7447.
    • J. Am. Chem. Soc. 2001, 123, 6801-6808.
    • Angew. Chem. Int. Ed. 2003, 3582-3603.
  • Lecture 3: Thursday, April 2rd - General Reactivity III
    • J. Org. Chem. 1999, 64, 1372-1374.
    • Synthesis 1973, 1-24.
    • Angew. Chem. Int. Ed. 2005, 376-393.
    • Directed Metalation: A Survival Guide (Krawczuk, 2008)
    • Haloselectivity in Heterocycles (Gutekunst, 2010)
  • Lecture 4: Monday, April 6th - Pyrroles
    • Indole & Pyrrole Synthesis: CliffsNotes (Richter, 2004)
  • Lecture 5: Tuesday, April 7th - Pyrroles/Furans/Thiophenes
    • Furans & Thiophene Synthesis: CliffsNotes (Shenvi, 2004)
    • Biotin (Shenvi, 2003)
    • Org. Proc. Res. Dev. 1999, 3, 56-59.
    • Org. Proc. Res. Dev. 2005, 9, 45-50.
    • Tetrahedron 1998, 54, 1955-2020.
    • Org. Proc. Res. Dev. 2002, 6, 357-366.
  • Lecture 6: Wednesday, April 8th - Indoles
  • Lecture 7: Thursday, April 9th - Indoles/Benzofurans
  • Review Session #1: Tuesday, April 21st
  • Lecture 8: Tuesday, April 28th - Pyridines
    • Pyridine Synthesis: CliffsNotes (O'Malley, 2004)
    • J. Am. Chem. Soc. 1958, 80, 4659-4670.
    • Chem. Rev. 1986, 86, 781-793.
    • Org. Lett. 2000, 2, 4201-4204.
    • Org. Lett. 2000, 2, 4205-4208.
    • Tet. Lett. 2002, 43, 4931-4933.
    • J. Med. Chem. 2005, 48, 3474-3477.
    • Advances in Heterocyclic Natural Product Synthesis
      1996, 3, 1-55 (no link available)
  • Lecture 9: Wednesday, April 29th - Pyridines/Quinolines
    • Org. Proc. Res. Dev. 1997, 1, 185-197.
    • Org. Proc. Res. Dev. 2002, 6, 242-245.
    • Org. Proc. Res. Dev. 2004, 8, 643-650.
    • J. Am. Chem. Soc. 1968, 90, 7102-7106.
    • J. Am. Chem. Soc. 1971, 93, 4074-4075.
    • J. Am. Chem. Soc. 1971, 93, 5575-5576.
    • J. Am. Chem. Soc. 1971, 93, 5576-5577.
    • Tetrahedron 2003, 59, 8649-8687.
    • J. Org. Chem. 1975, 40, 2140-2141.
    • Org. Lett. 2004, 6, 3-5.
    • Synthesis 2005, 339–360.
    • Advances in Heterocyclic Natural Product Synthesis
      1992, 2, 377-400 (no link available)
  • Lecture 10: Thusday, April 30st - Case Studies
    • Masterpieces in Process Chemistry (Richter, 2004)
  • Review Session #2:Monday, May 4th
    • [PROBLEM SET 1 DUE]
  • Midterm: Tuesday, May 5th
  • Lecture 11: Wednesday, May 6th - Pyryliums/Pyrones
    • J. Org. Chem. 2003, 68, 5967-5973.
    • Tet. Lett. 1990, 51, 7449-7452.
    • J. Med. Chem. 1985, 28, 1828-1832.
    • J. Med. Chem. 1996, 39, 1303-1313.
    • Org. Proc. Res. Dev. 1999, 3, 256-259.
    • Org. Proc. Res. Dev. 2000, 4, 488-497.
    • Org. Proc. Res. Dev. 2003, 7, 74-81.
    • Org. Proc. Res. Dev. 2004, 8, 897-902.
    • C & E News 2006, 84(18), 30-32.
  • Lecture 12: Thusday, May 7th - Di-, Tri-, and Tetrazines
    • Angew. Chem. Int. Ed. 1999, 38, 448-476.
    • J. Med. Chem. 2005, 48, 744-752.
    • The Biginelli and Related Reactions (DeMartino, 2003)
  • Lecture 13: Monday, May 11th - 1,3 Azoles
    • C & E News 2006, 84(14), 36-38.
    • Org. Proc. Res. Dev. 2001, 5, 37-44.
    • Org. Proc. Res. Dev. 2002, 6, 677-681.
    • J. Am. Chem. Soc. 1993, 115, 8449-8450.
    • J. Med. Chem. 2002, 45, 1511-1517.
    • Org. Lett. 2004, 6, 929-931.
    • J. Org. Chem. 1998, 63, 2800-2801.
  • Lecture 14: Wednesday, May 20th - 1,2 Azoles
    • Isoxazoles & Isothiazoles in Synthesis (Mitsos, 2004)
    • Org. Proc. Res. Dev. 1998, 2, 151-156.
    • Org. Proc. Res. Dev. 2001, 5, 587-592.
    • Org. Proc. Res. Dev. 2003, 7, 521-532.
    • Org. Proc. Res. Dev. 2005, 9, 88-97.
    • Org. Proc. Res. Dev. 2005, 9, 179-184.
    • J. Org. Chem. 2004, 69, 7058-7056.
    • Org. Lett. 2006, 8, 3505-3508.
    • Org. Lett. 2008, 10, 1307-1310.
  • Lecture 15: Thusday, May 21st - Azoles/Purines
  • Lecture 16: Tuesday, May 26th - Purines and Azole Case Studies
    • Org. Lett. 2003, 5, 2067-2070.
    • Org. Lett. 2003, 5, 2071-2074.
    • Org. Lett. 2004, 6, 3691-3694.
    • Org. Lett. 2005, 7, 2817-2820.
    • Nature 2009, 459, 239-242.
  • Lecture 17: Thusday, May 28th - Benzodiazepines
    • J. Med. Chem. 1979, 22, 1-7.
    • J. Med. Chem. 1988, 31, 2235-2246.
  • Lecture 18: Monday, June 1st - Alkaloid Biosynthesis 101
    • J. Org. Chem. 2003, 68, 2529-2539.
    • Nat. Prod. Rep. 2004, 21, 224-248.
    • Indolizidine Alkaloids (Richter, 2006)
    • Morphine and Codeine (Li, 2005)
    • Ernest Wenkert (DeMartino, 2005)
    • Delphinine Alkaloids (Ambhaikar, 2004)
    • Vindoline (Mitsos, 2004)
    • Acridine Alkaloids (Lockner, 2006)
    • Isoquinoline Alkaloids (Shi, 2006)
    • Ajmaline and Sarpagine Alkaloids (Newhouse, 2006)
    • Discorhabdin Alkaloids (Krawczuk, 2006)
    • Lupin Alkaloids (Seiple, 2006)
    • Stemona Alkaloids (Maimone, 2006)
  • Lecture 19: Tuesday, June 2rd - Bridging and Exotic Heterocycles
    • Angew. Chem. Int. Ed. 2003, 42, 2010-2023.
    • J. Am. Chem. Soc. 2005, 127, 15038-15039.
    • Org. Proc. Res. Dev. 1998, 2, 175-185.
    • Org. Proc. Res. Dev. 2006, 10, 257-261.
    • J. Med. Chem. 2004, 47, 1-9.
    • J. Am. Chem. Soc. 2006, 128, 8087-8094.
  • Lecture 20: Wednesday, June 3rd - Heterocyclic Potpourri
    • Masterpieces in Process Chemistry-II (Richter, 2006)
  • Lecture 21: Thusday, June 4th - Heterocyclic Millionaire-[PROBLEM SET 2 DUE
  • Review Session #3: Monday, June 8th
    • Who Wants to be a Heterocyclic Millionaire!
  • Final: Tuesday, June 9th
    • [PROJECT DUE]

2015

   
  • Grades: Midterm (30%), Final (30%), Problem Sets/Project (30%), Class Participation (10%) 
    Examples:
    • 2005 Midterm2005 Final2005 Problem Set
    • 2006 Midterm2006 Final2006 Problem Set
    • 2007 Midterm2007 Final2007 Problem Set
    • 2008 Midterm2008 Final2008 Problem Set
    • 2009 Midterm2009 Final2009 Problem Set 12009 Problem Set 2
    • 2011 Midterm2011 Final2011 Problem Set 12011 Problem Set 2
  • Midterm and Final are open note exams, 2 hours
    Definition of "open notes": Only handwritten notes (from lectures and any other source), no copies allowed. Lecture summaries are the only handouts permitted during test.
  • Heteroaromatic Transformations Project: Review a heteroaromatic transformation and compose a 1-page written synopsis as well as a 1-page graphical summary of transformations. Examples will be provided. 

 

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