Advisee Information
Chemii Club
Courses Taught
 • FS 101
 • Chem 110
 • Chem 112
 • Chem 231
 • Chem 232
 • Chem 236
 • Chem 434
 • Chem 587
 • Chem 590
 • Chem 611/612
Inside Chemistry
Master Calendar
Organic Workshops
Pelletier Library
Registration Information
Research and CV
Schedule
Web Links

Allegheny College
Department of Chemistry
520 N. Main Street
Meadville, PA 16335
814-332-5363

Chem 434: Readings

(to be done before each class)










Make an Office Appointment

Overview
  1. Mann, Chapter 1 (pp. 1-9).
Mevalonic acid pathway
  1. Mann, Chapter 4a (pp. 31-40)
  2. Dewick, P.M., "The biosynthesis of C5-C25 terpenoid compounds", Nat. Prod. Rep. 1999, 14(2), 97-104.
Terpenoid biosynthesis
  1. Mann, Chapter 4b (pp. 40-52)
  2. Bohlmann, J.; Keeling, C.I., "Terpenoid biomaterials", The Plant Journal 2008, 54, 656-669.
Steroid biosynthesis
  1. Bloch, K., "The biological synthesis of cholesterol", Science 1965, 150, 19-28.
  2. Ajikumar, P.K.; Tyo, K.; Carlsen, S.; Mucha, O.; Phon, T.H.; Stephanopoulos, G., "Terpenoids: opportunities for biosynthesis of natural product drugs using engineered microorganisms", Mol. Pharmaceutics 2008, 5(2), 167-178.
Early total synthesis of steroids
  1. Mulheirn, G., "Robinson, Woodward and the synthesis of cholesterol", Endeavour 2000, 24(3), 107-110.
  2. Stork, G.; McMurry, J.E., "Stereospecific total synthesis of steroids via isoxazole annelation. dl-D-Homotestosterone and dl-progesterone", J. Am. Chem. Soc. 1967, 89, 5464-5465.
  3. Grieco, P.A.; Takigawa, T.; Schillinger, W.J., "Bicyclo[2.2.1]heptanes as intermediates in the synthesis of steroids. Total synthesis of estrone", J. Org. Chem. 1980, 45, 2247-2251.
Biomimetic synthesis of steroids
  1. Johnson, W.S.; Gravestock, M.B.; McCarry, B.E., "Acetylenic bond participation in biogenetic-like
    olefinic cyclizations. II. Synthesis of dl-progesterone", J. Am. Chem. Soc. 1971, 93, 4332-4334.
  2. Fish, P.V.; Johnson, W.S., "The first examples of nonenzymic, biomimetic polyene pentacyclizations. Total synthesis of the pentacyclic triterpenoid sophoradiol", J. Org. Chem. 1994, 59, 2324-2335.
  3. Corey, E.J.; Lin, S., "A short enantioselective toal synthesis of Dammarenediol II", J. Am. Chem. Soc. 1996, 118, 8765-8766.
Contemporary steroid total synthesis
  1. Pattenden, G.; Reddy, L.K.; Walter, A., "A new total synthesis of (±)-oestrone", Tetrahedron Lett. 2004, 45, 4027-4030.
  2. Hu, Q.-Y.; Rege, P.D.; Corey, E.J., "Simple, catalytic enantioselective syntheses of estrone and desogestrel", J. Am. Chem. Soc. 2004, 126, 5984-5986
  3. Nicolaou, K.C.; Sun, Y.-P.; Peng, X.-S.; Polet, D.; Chen, D.Y.-K., "Total synthesis of (+)-Cortistatin A", Ang. Chem. Int. Ed. 2008, 47, 7310-7313.
  4. Shenvi, R.A.; Guerrero, C.A.; Shi, J.; Li, C.-C.; Baran, P.S., "Synthesis of (+)-Cortistatin A", J. Am. Chem. Soc. 2008, 130, 7241-7243.
  5. Honma, M.; Nakada, M., "Enantioselective total synthesis of (+)-digitoxigenin", Tetrahedron Lett. 2007, 48, 1541-1544.
Papers covered in student presentations
  1. TBA
  2. TBA
  3. TBA
  4. TBA
  5. TBA
  6. TBA
  7. TBA

Important: this page is continually updated!


Advanced Search