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Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja4023557DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja4023557PublisherArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3662218/PubMed CentralArticle
ORCID:
AuthorORCID
Chuang, Kangway V.0000-0002-0652-8071
Reisman, Sarah E.0000-0001-8244-9300
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.
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
Alfred P. Sloan FoundationUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
CaltechUNSPECIFIED
AmgenUNSPECIFIED
DuPontUNSPECIFIED
NIHRGM097582A
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: Jason Perez
Deposited On:03 Jun 2013 22:47
Last Modified:09 Nov 2021 23:39

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