Krishnan, Shyam and Bagdanoff, Jeffrey T. and Ebner, David C. and Ramtohul, Yeeman K. and Tambar, Uttam K. and Stoltz, Brian M. (2008) Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: Applications to the total synthesis of alkaloids. Journal of the American Chemical Society, 130 (41). pp. 13745-13754. ISSN 0002-7863 http://resolver.caltech.edu/CaltechAUTHORS:KRIjacs08
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Abstract
Enantioselective syntheses of the alkaloids (-)-aurantioclavine, (+)-amurensinine, (-)-lobeline, and (-)- and (+)-sedamine are described. The syntheses demonstrate the effectiveness of the Pd-catalyzed asymmetric oxidation of secondary alcohols in diverse contexts and the ability of this methodology to set the absolute configuration of multiple stereocenters in a single operation. The utility of an aryne C-C insertion reaction in accessing complex polycyclic frameworks is also described.
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| Additional Information: | © 2008 American Chemical Society. Received June 20, 2008. The authors thank the NIH-NIGMS (R01 GM65961-01), California TRDRP (postdoctoral fellowships to Y.K.R. and S.K., and predoctoral fellowship to J.T.B.), NDSEG (predoctoral fellowships to D.C.E. and U.K.T.), NSF (predoctoral fellowship to D.C.E.), Caltech, AstraZeneca, Boehringer Ingelheim, Johnson & Johnson, Pfizer, Merck, Amgen, Abbott, Research Corporation, Roche, and GlaxoSmithKline for generous funding | ||||||||||||||
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| Subject Keywords: | Amino-acid derivatives; asymmetric-synthesis; kinetic resolution; lobelia alkaloids; Molecular-oxygen; tert-butanesulfinamide; coupling reactions; C-H; insertion; cyclization | ||||||||||||||
| Record Number: | CaltechAUTHORS:KRIjacs08 | ||||||||||||||
| Persistent URL: | http://resolver.caltech.edu/CaltechAUTHORS:KRIjacs08 | ||||||||||||||
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| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||
| ID Code: | 13587 | ||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||
| Deposited By: | Tony Diaz | ||||||||||||||
| Deposited On: | 12 May 2009 19:29 | ||||||||||||||
| Last Modified: | 26 Dec 2012 10:52 |
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