Kieffer, Madeleine E. and Chuang, Kangway V. and Reisman, Sarah E. (2013) Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B. Journal of the American Chemical Society, 135 (15). pp. 5557-5560. ISSN 0002-7863. PMCID PMC3662218. doi:10.1021/ja4023557. https://resolver.caltech.edu/CaltechAUTHORS:20130603-133349209
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Abstract
A copper-catalyzed arylation of tryptophan derivatives is reported. The reaction proceeds with high site- and diastereoselectivity to provide aryl pyrroloindoline products in one step from simple starting materials. The utility of this transformation is highlighted in the five-step syntheses of the natural products (+)-naseseazine A and B.
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| Additional Information: | © 2013 American Chemical Society. Received: March 6, 2013; Published: March 29, 2013. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment and Dr. Matthew Winston for samples of L6. We also thank Sigma-Aldrich for a kind donation of chemicals. Fellowship support was provided by the National Science Foundation (Graduate Research Fellowships to M.E.K. and K.V.C., Grant DGE-1144469). S.E.R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Financial support from the California Institute of Technology, Amgen, DuPont, and the NIH(NIGMS RGM097582A) is gratefully acknowledged. | ||||||||||||||||
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| Issue or Number: | 15 | ||||||||||||||||
| PubMed Central ID: | PMC3662218 | ||||||||||||||||
| DOI: | 10.1021/ja4023557 | ||||||||||||||||
| Record Number: | CaltechAUTHORS:20130603-133349209 | ||||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20130603-133349209 | ||||||||||||||||
| Official Citation: | Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B Madeleine E. Kieffer, Kangway V. Chuang, and Sarah E. Reisman Journal of the American Chemical Society 2013 135 (15), 5557-5560 | ||||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||||
| ID Code: | 38761 | ||||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||||
| Deposited By: | INVALID USER | ||||||||||||||||
| Deposited On: | 03 Jun 2013 22:47 | ||||||||||||||||
| Last Modified: | 09 Nov 2021 23:39 |
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