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Total synthesis and stereochemical revision of (+)-aeruginosin 298-A

Wipf, P and Methot, JL (2000) Total synthesis and stereochemical revision of (+)-aeruginosin 298-A. Organic Letters, 2 (26). 4213 - 4216. ISSN 1523-7060

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Abstract

(aquation presented) Novel routes toward both enantiomers of the bicyclic proline surrogate 2-carboxy-6-hydroxyoctahydroindole, i.e., Choi, were developed on the basis of the oxidative cyclization of L-tyrosine. Synthesis of the proposed sequence of (+)-aeruginosin 298-A did not provide the natural product. Incorporation of a D-leucine residue, in contrast, led to the total synthesis of this thrombin inhibitor.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Methot, JL
Date: 28 December 2000
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 2
Number: 26
Page Range: 4213 - 4216
DOI or Unique Handle: 10.1021/ol006759x
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
MeSH Headings: Antithrombins--chemical synthesis; Antithrombins--chemistry; Leucine--analogs & derivatives; Leucine--chemical synthesis; Leucine--chemistry; Oxidation-Reduction; Stereoisomerism
PubMed ID: 11150202
Date Deposited: 21 Feb 2014 21:10
Last Modified: 02 Feb 2019 15:56
URI: http://d-scholarship.pitt.edu/id/eprint/20544

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