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:	Creators Email Pitt Username ORCID Wipf, P pwipf@pitt.edu PWIPF 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-dev.library.pitt.edu/id/eprint/20544

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