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Issue 14, 2004
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Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula

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Abstract

(+)-Kalkitoxin, a metabolite of the marine cyanobacterium Lyngbya majuscula, was synthesized from (R)-2-methylbutyric acid, (R)-cysteine, and (3S, 4S, 6S)-3,4,6-trimethyl-8-(methylamino)octanoic acid. A key step in the synthesis was installation of the anti,anti methyl stereotriad by means of a tandem asymmetric conjugate addition of an organocopper species to an α,β-unsaturated N-acyl oxazolidin-2-one followed in situ by α-methylation of the resultant enolate. The thiazoline portion of kalkitoxin was assembled by titanium tetrachloride catalyzed cyclization of a vinyl substituted amido thiol.

Graphical abstract: Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula

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Publication details

The article was received on 19 Mar 2004, accepted on 30 Apr 2004 and first published on 28 Jun 2004


Article type: Paper
DOI: 10.1039/B404205K
Citation: Org. Biomol. Chem., 2004,2, 2092-2102
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    Total synthesis and biological evaluation of (+)-kalkitoxin, a cytotoxic metabolite of the cyanobacterium Lyngbya majuscula

    J. D. White, Q. Xu, C. Lee and F. A. Valeriote, Org. Biomol. Chem., 2004, 2, 2092
    DOI: 10.1039/B404205K

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