Beecher, Jody E. and Tirrell, David A. (1998) Synthesis of protected derivatives of 3-pyrrolylalanine. Tetrahedron Letters, 39 (23). pp. 3927-3930. ISSN 0040-4039. doi:10.1016/S0040-4039(98)00722-9. https://resolver.caltech.edu/CaltechAUTHORS:BEEtl1998
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Abstract
Protected derivatives of 3-pyrrolylalanine (3-PA) have been synthesized starting with N-tri(isopropyl)silylpyrrole. Following formylation and Boc protection, treatment with (±)-N-(benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester provided a fully protected dehydro-3-pyrrolylalanine. Reduction of the double bond and removal of the methyl ester groups yielded 3-PA protected at the α- and pyrrole nitrogens. 3-PA is only transiently stable following N-deprotection.
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| Additional Information: | © 1998 Elsevier. Received 27 February 1998; revised 24 March 1998; accepted 1 April 1998. This work was supported by a grant from the Polymers and Genetics Programs of the National Science Foundation. NMR spectra were recorded in the University of Massachusetts NMR Laboratory, which is supported by the NSF Materials Research Laboratory at the University. Jody Beecher thanks the National Institutes of Health for financial support of her postdoctoral research. | |||||||||
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| Issue or Number: | 23 | |||||||||
| DOI: | 10.1016/S0040-4039(98)00722-9 | |||||||||
| Record Number: | CaltechAUTHORS:BEEtl1998 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:BEEtl1998 | |||||||||
| Official Citation: | Jody E. Beecher, David A. Tirrell, Synthesis of protected derivatives of 3-pyrrolylalanine, Tetrahedron Letters, Volume 39, Issue 23, 4 June 1998, Pages 3927-3930, ISSN 0040-4039, http://dx.doi.org/10.1016/S0040-4039(98)00722-9. (http://www.sciencedirect.com/science/article/pii/S0040403998007229) | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 53436 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Anne Hormann | |||||||||
| Deposited On: | 02 Feb 2015 04:57 | |||||||||
| Last Modified: | 10 Nov 2021 20:02 |
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