CaltechAUTHORS
  A Caltech Library Service

Synthesis of protected derivatives of 3-pyrrolylalanine

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. https://resolver.caltech.edu/CaltechAUTHORS:BEEtl1998

Full text is not posted in this repository. Consult Related URLs below.

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:BEEtl1998

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1016/S0040-4039(98)00722-9DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403998007229PublisherArticle
ORCID:
AuthorORCID
Tirrell, David A.0000-0003-3175-4596
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.
Funders:
Funding AgencyGrant Number
NSFUNSPECIFIED
NIH Postdoctoral FellowshipUNSPECIFIED
Issue or Number:23
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:03 Oct 2019 07:49

Repository Staff Only: item control page