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Heterocyclic Chemistry Class

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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:
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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Heterocyclic Chemistry Class

2015