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lecture 14 - FK506-FKBP Complex Structure Van Duyne G D...

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O O O O N Me OMe OH H MeO MeO Me Me OH Me H O Me H OH O FK506 R OR''' OH O R' R" R OR''' O O R' R" R OR' OH O R" R OR' OH O HO O I R O R EtO OH R EtO OH R OH EtO 2 C HO O I R HO OH R Cl OAc S S R MeO R OMe Chem 215 Lecture 14: Organic Synthesis with the Goal of Exploring the Cellular Mechanism of FK506. Wednesday, November 7, 2007 Reading Assignment: SANROS pp 10-11, 204-205, 382-383, 490-491. Syntheses Discussed: References: FK506 Synthesis: Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990 , 112 , 5583-5601. FK506 Biological Mechanism: Rosen, M. K.; Standaert, R. F.; Galat, A.; Nakatsuka, M.; Schreiber, S. L. Science . 1990 , 248 (4957), 863-866.
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Unformatted text preview: FK506-FKBP Complex Structure: Van Duyne, G. D.; Standaert, R. F.; Karplus, P. A.; Schreiber, S. L.; Clardy, J. . 1991 , 252 (5007), 839-842. Partial List of Transforms Covered: Noyori Asymmetric Hydrogenation Reaction Frater-Seebach Alkylation Iodoetherification Reductive Cleavage of Iodoethers Opening of Epoxides with the Lithium Ethoxyacetylide Oxymercuration of Ynones to form Esters Gilbert-Seyferth Reagent Moffatt Reagent Dimethylacetals from Dithianes using the Stork Reagent Graphical Transform Guide: Shair RCHO R H...
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