Synthesis and structure of mycolactone e isolated from frog mycobacterium

Organic Letters

Volumn 10, Issue 23, 2008, Pages 5385-5388

  Aubry, Sylvain ^a   Lee, Richard E ^b   Mahrous, Engy A ^b   Small, Pam L C ^c   Beachboard, Dia ^c   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

^b UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^c UNIVERSITY OF TENNESSEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE; MYCOLACTONE E; UNSATURATED FATTY ACID;

ANIMAL; ARTICLE; CHEMISTRY; FROGS AND TOADS; HUMAN; ISOLATION AND PURIFICATION; MICROBIOLOGY; MYCOBACTERIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TANDEM MASS SPECTROMETRY; ANURA;

ANIMALS; ANURA; FATTY ACIDS, UNSATURATED; HUMANS; LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MYCOBACTERIUM; TANDEM MASS SPECTROMETRY;

EID: 61349164855     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802233f     Document Type: Article

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23. The core alcohol 5 was synthesized by Dr. Han-Je Kim in this laboratory.
24. The lipid extract from fermentation broth of M. liflandii was used for this work. The amount of mycolactone E in this extract was estimated to be equivalent with ∼10 injections for HPLC analysis.
25. See Supporting Information.
26. 1H NMR comparison (vide infra).
27. 1H NMR spectrum ever recorded on natural mycolactone E.
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30. For the mycolactone F case, a mixture of isopropanol and toluene was used as an eluting solvent. The HPLC profile in two solvent systems is significantly different. For the details, see Supporting Information.