Steps to Synthetic Planning

Steps to Synthetic Planning - Diels-Alder Reaction[2 2...

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OH O Shair Chem 215 Lecture 1: Steps to Synthetic Planning Monday, September 17, 2007 Reading Assignment: Corey & Cheng Ch 1-3; Handout: Reduction; SANROS pp 44-47, 140-141, 186-187, 308-309, 486-489, 496-497 References: Endiandric Acids A and B: Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E.; Uenishi, J. J. Am. Chem. Soc . 1982 , 104 , 5555-5557. Nicolaou, K. C.; Zipkin, R. E.; Petasis, N. A. J . Am. Chem. Soc . 1982 , , 5558-5560. Nicolaou, K. C.; Petasis, N. A.; Zipkin, R. E. J. Am. Chem. Soc. 1982 , , 5560-5562. Diels-Alder Reaction in Synthesis: Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem., Int. Ed. Engl . 2002 , 41 , 1668-1698. Graphical Transform Guide: Syntheses Discussed: R R R H Partial List of Transforms Covered:
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Unformatted text preview: Diels-Alder Reaction [2+2] Photocycloaddition C=O Reduction Wittig Reduction Syn Opening of Epoxides with LiNEt 2 Ketal Hydrolysis C=C Oxidative Cleavage Nef Reaction C=C Reduction Barton Deoxygenation Barton Decarboxylation Wolff-Kishner Reduction Nitroalkane Reduction Glaser Coupling Reaction Lindlar Reduction 1,3,5-Hexatriene Electrocyclization 1,3,5,7-Octatetraene Electrocyclization H H H H Ph H CO 2 H n Endiandric Acid A, n = 0 Endiandric Acid B, n = 1 Partial List of Topics Discussed: • Transform • Retron • Part Retron • Full Retron • Functional Group Interconversions 2 O Ph 3 P n OH n O O O H H O OR OR H OH H CO 2 H H H O H NO 2 R R 1 R R 1 H O NO 2...
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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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