Published April 17, 2013
| Supplemental Material + Accepted Version
Journal Article
Open
Copper-Catalyzed Diastereoselective Arylation of Tryptophan Derivatives: Total Synthesis of (+)-Naseseazines A and B
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.
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.Attached Files
Accepted Version - nihms-463043.pdf
Supplemental Material - ja4023557_si_001.pdf
Supplemental Material - ja4023557_si_002.pdf
Files
ja4023557_si_001.pdf
Additional details
- PMCID
- PMC3662218
- Eprint ID
- 38761
- DOI
- 10.1021/ja4023557
- Resolver ID
- CaltechAUTHORS:20130603-133349209
- DGE-1144469
- NSF Graduate Research Fellowship
- Alfred P. Sloan Foundation
- Camille and Henry Dreyfus Foundation
- Caltech
- Amgen
- DuPont
- RGM097582A
- NIH
- Created
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2013-06-03Created from EPrint's datestamp field
- Updated
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2021-11-09Created from EPrint's last_modified field