Mechanistic Development of Transforms

Mechanistic Development of Transforms - J. Am. Chem. Soc ....

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Shair Chem 215 Lecture 4: Mechanistic Development of Transforms Wednesday, September 26, 2007 SANROS pp 28-29, 38-39, 116-117, 130-133, 190-191, 384-385, 444-445. Partial List of Topics Discussed: • Mechanistic Development of Transforms • Introduction to the Cation-Olefin Cyclization • Topological Strategies-Rearrangement and Connective Transforms Partial List of Transforms Covered: Cation-Olefin Cyclization Alcohol Dehydration 1,2-C-C Shift Vinyl Cyclopropane Rearrangement Carbenoid-Mediated Cyclopropanation Electrophilic Bromonation E2 Elimination Sodium Chlorite Oxidation of Aldehydes to Carboxylic Acids Eschenmoser's Salt Favorskii Rearrangement References: Progesterone: Johnson, W. S.; Gravestock, M. B.; McCarry, B. E. J. Am. Chem. Soc . 1971 , 93 , 4332- 4334. Gravestock, M. B.; Johnson, W. S.; McCarry, B. E.; Parry, R. J.; Ratcliffe, B. E.
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Unformatted text preview: J. Am. Chem. Soc . 1978 , 100 , 4274-4282. Antheridic Acid: Corey, E. J.; Myers, A. G. . 1985 , 107 , 5574-5576. -Caryophyllene Alcohol: Corey, E. J.; Nozoe, S. J. Am. Chem. Soc. 1964 , 86 , 1652-1653. Corey, E. J.; Nozoe, S. . 1965 , 87 , 5733-5735. Isocomene: Pirrung, M. C. . 1979 , 101 , 7130-7131. Cubane: Eaton, P. E.; Cole, T. W., Jr. . 1964 , , 962-964. Eaton, P. E.; Cole, T. W., Jr. . 1964 , , 3157-3158. Syntheses Discussed: Graphical Transform Guide: O Me O H H H Me H Me Progesterone Me Me H OH H H Me Me -Caryophyllene Alcohol Me Me Me Me Isocomene CO 2 H O O OH Me HO Antheridic Acid Cubane X n n R OH R' R" R R' OH R" R' R O R O R' N 2 Br Br X H R OH O R H O O O HO O R' R R O R' X R O R' OR''' O R X R M...
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This note was uploaded on 04/07/2008 for the course CHEM 215 taught by Professor Shair during the Fall '07 term at Harvard.

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