Heterocyclic Chemistry at The Scripps Research Institute

Lecture 1: Monday, April 9th - General Reactivity I
- J. Org. Chem. 1994, 59, 3656-3664.
- Eur. J. Org. Chem. 2002, 4095-4122.
Lecture 2: Thursday, April 12th - 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: Friday, April 13th - General Reactivity III
- J. Org. Chem. 1999, 64, 1372-1374.
- Synthesis, 1973, 1-24.
- Angew. Chem. Int. Ed. 2005, 373-393.
Lecture 4: Tuesday, April 17th - Pyrroles

Indole & Pyrrole Synthesis: Cliff Notes (Richter, 2004)

Lecture 5: Monday, April 23th - Pyrroles/Furans/Thiophenes
- Furans & Thiophene Synthesis: Cliff Notes (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: Tuesday, April 24th - Indoles
Lecture 7: Wednesday, April 25th - Indoles/Benzofurans
Lecture 8: Thursday, April 26th - Pyridines
- Pyridine Synthesis: Cliff Notes (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: Friday, April 27th - 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, 2140-2140.
- 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: Tuesday, May 1st - Case Studies
- Masterpieces in Process Chemistry (Richter, 2004)
Review Session: Thursday, May 3rd
Midterm: Saturday, May 5th (in Keck, 10am)
- [PROBLEM SET 1 DUE]
Lecture 11: Monday, May 7th - 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.
Lecture 12: Tuesday, May 8th - Di-, Tri-, and Tetrazines
- Angew. Chem. Int. Ed. 1999, 38, 448-478.
- J. Med. Chem. 2005, 48 744-752.
- The Biginelli and Related Reactions (Demartino, 2003)
Lecture 13: Wednesday, May 9th - 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: Thursday, May 10th - 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.
Special Guest Lecture: Friday, May 11th Victor Snieckus
- Ph.D., Queens University
Lecture 15: Thursday, May 17th - Azoles/Purines
Lecture 16: Monday, May 21st - 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.
Lecture 17: Tuesday, May 22nd - Benzodiazepines
- J. Med. Chem. 1979 , 22, 1-7.
- J. Med. Chem. 1988, 31, 2235-2246.
Lecture 18: Tuesday, May 29th - Alkaloid Biosynthesis 101
- J. Org. Chem., 2003, 68, 2529-2539.
- Nat. Prod. Rep., 2004, 21, 224 - 248.
- Indolizidine Alkaloids (Jeremy, 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: Thursday, May 31st - Heterocyclic Potpourri
- 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: Tuesday, June 5th - Review
- Masterpieces in Process Chemistry-II (Richter, 2006)
Special Guest Lecture: Friday, June 8th Dr. Robert Waltermire, BMS Process Group
Final: Tuesday, June 12th - [Heterocycles in Medicine Summary DUE]

Professor Phil Baran email: pbaran@scripps.edu website TAs: Jeremy Richter, BCC-169, 784-7371 email: jrichter@scripps.edu Benjamin Hafensteiner , BCC-169, 784-7371 email: benhaf@scripps.edu	Texts: Joule and Mills, "Heterocyclic Chemistry" Li, "Name Reactions in Heterocyclic Chemistry" Time: M/W/F 8:15-9:45 am, T/Th 10:00 - 11:30 am Location: Beckman Lecture Hall (BCC-1) Syllabus (pdf) Essentials of Heterocyclic Chemistry I Essentials of Heterocyclic Chemistry II Essentials of Heterocyclic Chemistry III
	2007
Lecture 1: Monday, April 9th - General Reactivity I J. Org. Chem. 1994, 59, 3656-3664. Eur. J. Org. Chem. 2002, 4095-4122. Lecture 2: Thursday, April 12th - 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: Friday, April 13th - General Reactivity III J. Org. Chem. 1999, 64, 1372-1374. Synthesis, 1973, 1-24. Angew. Chem. Int. Ed. 2005, 373-393. Lecture 4: Tuesday, April 17th - Pyrroles Indole & Pyrrole Synthesis: Cliff Notes (Richter, 2004) Lecture 5: Monday, April 23th - Pyrroles/Furans/Thiophenes Furans & Thiophene Synthesis: Cliff Notes (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: Tuesday, April 24th - Indoles Lecture 7: Wednesday, April 25th - Indoles/Benzofurans Lecture 8: Thursday, April 26th - Pyridines Pyridine Synthesis: Cliff Notes (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: Friday, April 27th - 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, 2140-2140. 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: Tuesday, May 1st - Case Studies Masterpieces in Process Chemistry (Richter, 2004) Review Session: Thursday, May 3rd Midterm: Saturday, May 5th (in Keck, 10am) [PROBLEM SET 1 DUE] Lecture 11: Monday, May 7th - 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: Tuesday, May 8th - Di-, Tri-, and Tetrazines Angew. Chem. Int. Ed. 1999, 38, 448-478. J. Med. Chem. 2005, 48 744-752. The Biginelli and Related Reactions (Demartino, 2003) Lecture 13: Wednesday, May 9th - 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: Thursday, May 10th - 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. Special Guest Lecture: Friday, May 11th Victor Snieckus Ph.D., Queens University Lecture 15: Thursday, May 17th - Azoles/Purines Lecture 16: Monday, May 21st - 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. Lecture 17: Tuesday, May 22nd - Benzodiazepines J. Med. Chem. 1979 , 22, 1-7. J. Med. Chem. 1988, 31, 2235-2246. Lecture 18: Tuesday, May 29th - Alkaloid Biosynthesis 101 J. Org. Chem., 2003, 68, 2529-2539. Nat. Prod. Rep., 2004, 21, 224 - 248. Indolizidine Alkaloids (Jeremy, 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: Thursday, May 31st - Heterocyclic Potpourri 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: Tuesday, June 5th - Review Masterpieces in Process Chemistry-II (Richter, 2006) Special Guest Lecture: Friday, June 8th Dr. Robert Waltermire, BMS Process Group Final: Tuesday, June 12th - [Heterocycles in Medicine Summary DUE]