Transform-Based Retrosynthetic Analysis

Transform-Based Retrosynthetic Analysis - D. M.; Shankaran,...

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Shair Chem 215 Lecture 2: Transform-Based Retrosynthetic Analysis Wednesday, September 19, 2007 References: Marasmic Acid: Greenlee, W. J.; Woodward, R. B. J. Am. Chem. Soc . 1976 , 98 , 6075-6076. Greenlee, W. J.; Woodward, R. B. Tetrahedron 1980 , 36 , 3367-3375. Boeckman, R. K., Jr.; Ko S. S. . 1980 , 102 , 7146-7149. FR182877: Evans, D. A.; Starr, J. T. Angew. Chem., Int. Ed. Engl . 2002 , 41 , 1787-1790. Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. . 2002, 124 , 4552-4553. Indanomycin: Roush, W. R.; Peseckis, S. M.; Walts, A. E. J. Org. Chem . 1984 , 49 , 3429-3432. Roush, W. R.; Myers, A. G. . 1981 , 46 , 1509-1511. Nicolaou, K. C.; Papahatjis, D. P.; Claremon, D. A.; Magolda, R. L.; Dolle, R. E. J. Org. Chem . 1985 , 50 , 1440-1456. Burke, S. D.; Piscopio, A. D.; Kort, M. E.; Matulenko, M. A.; Parker, M. H.; Armistead,
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Unformatted text preview: D. M.; Shankaran, K. . 1994 , 59 , 332-347. Graphical Transform Guide: Syntheses Discussed: Partial List of Transforms Covered: Wittig Reaction with Stabilized Ylides Desaturation by Selenoxide Elimination Alkylative Cyclopropanation Reduction of Lactones to Lactols Lactonization Oxidation of Alcohols to Aldehydes Enone Isomerization Reading Assignment: Corey & Cheng, Chapters 1-3. SANROS pp 8-9, 50-51, 102-103, 172-173, 266-267, 362-363. O O HO OHC H H Me Me Marasmic Acid O O O H Me Me OH HO H H H Me H O N H Et O HO 2 C H H H H Indanomycin R W O O O O W W X O O O OH O O HO CO 2 R RCHO RCH 2 OH O R Ph 3 P H W FR182877 Et Me Me Me...
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