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Establishment of the absolute configuration of the bioactive marine alkaloid eudistomin X by stereospecific synthesis

Citation

Finlayson, R and Brackovic, A and Simon-Levert, A and Banaigs, B and O'Toole, RF and Miller, CH and Copp, BR, Establishment of the absolute configuration of the bioactive marine alkaloid eudistomin X by stereospecific synthesis, Tetrahedron Letters: International Journal for The Rapid Publication of Preliminary Communications in Organic Chemistry, 52, (7) pp. 837-840. ISSN 0040-4039 (2011) [Refereed Article]

DOI: doi:10.1016/j.tetlet.2010.12.052

Abstract

The marine β-carboline alkaloid eudistomin X has been synthesised stereospecifically, using d-phenylalanine as the chiral pool starting material, establishing the absolute configuration of the natural product as (10R). A stereospecific synthesis of both enantiomers of the marine alkaloid eudistomin X using the amino acid chiral pool is achieved. Comparison of 1H and 13C NMR chemical shifts of the synthetic product as either the free base, mono-salt or disalt with those reported for the natural product established that the ascidian metabolite was originally characterised as a mono-salt and that the absolute configuration was (10R).

Item Details

Item Type:Refereed Article
Keywords:β-Carboline; Ascidian; Biological activity; Chiral pool; Marine alkaloid; Stereospecific synthesis
Research Division:Biological Sciences
Research Group:Microbiology
Research Field:Bacteriology
Objective Division:Health
Objective Group:Clinical Health (Organs, Diseases and Abnormal Conditions)
Objective Field:Infectious Diseases
Author:O'Toole, RF (Dr Ronan O'Toole)
ID Code:95704
Year Published:2011
Web of Science® Times Cited:7
Deposited By:Medicine (Discipline)
Deposited On:2014-10-07
Last Modified:2017-11-06
Downloads:0

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