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Establishment of the absolute configuration of the bioactive marine alkaloid eudistomin X by stereospecific synthesis
journal contribution
posted on 2023-05-18, 04:14 authored by Finlayson, R, Brackovic, A, Simon-Levert, A, Banaigs, B, O'Toole, RF, Miller, CH, Copp, BRThe 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).
History
Publication title
Tetrahedron Letters: International Journal for The Rapid Publication of Preliminary Communications in Organic ChemistryVolume
52Issue
7Pagination
837-840ISSN
0040-4039Department/School
Tasmanian School of MedicinePublisher
Pergamon-Elsevier Science LtdPlace of publication
The Boulevard, Langford Lane, Kidlington, Oxford, England, Ox5 1GbRepository Status
- Restricted