Structure revision of trichotoxin, a chlorinated polyketide isolated from a Trichodesmium thiebautii bloom

Tetrahedron Letters
Matthew J BertinPeter D R Moeller

Abstract

NMR-guided fractionation of the lipophilic extract of Trichodesmium thiebautii filaments led to the isolation of a phenyl-containing chlorinated polyketide (1) and an alkyne-containing analogue (2). Comparison of spectroscopic and spectrometric data of 1 with the data of the previously reported trichotoxin, strongly suggested that these metabolites were identical and supports a structural revision of trichotoxin and its designation as trichotoxin A. In addition, we report the isolation and characterization of the alkyne-containing analogue trichotoxin B (2). Absolute configuration of 1 and 2 is proposed based on spectroscopic comparison to a close structural analog.

Citations

Jan 13, 2017·Natural Product Reports·Robert A Hill, Andrew Sutherland
Aug 21, 2020·Journal of Natural Products·Kelly M McManusMatthew J Bertin

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