Overview
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Mann, Chapter 1 (pp. 1-9).
Mevalonic acid pathway
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Mann, Chapter 4a (pp. 31-40)
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Dewick, P.M., "The biosynthesis of C5-C25
terpenoid compounds", Nat. Prod. Rep. 1999, 14(2),
97-104.
Terpenoid biosynthesis
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Mann, Chapter 4b (pp. 40-52)
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Bohlmann, J.; Keeling, C.I., "Terpenoid biomaterials", The
Plant Journal 2008, 54, 656-669.
Steroid biosynthesis
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Bloch, K., "The biological synthesis of cholesterol", Science
1965, 150, 19-28.
- 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
- Mulheirn, G., "Robinson, Woodward and the synthesis of cholesterol",
Endeavour 2000, 24(3), 107-110.
- 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.
- 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
- 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.
- 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.
- 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
- Pattenden, G.; Reddy, L.K.; Walter, A., "A new total synthesis
of (±)-oestrone", Tetrahedron Lett. 2004,
45, 4027-4030.
- 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
- 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.
- 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.
- Honma, M.; Nakada, M., "Enantioselective total synthesis of (+)-digitoxigenin",
Tetrahedron Lett. 2007, 48, 1541-1544.
Papers covered in student presentations
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