Arbeitskreis Lindel
Marine Naturstoffe - Bausteine des Lebens
Have you thought about organic synthesis lately?
Aktuelle Publikationen:
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Inhalt:
Shine light on your chemistry! Irradiating 3-(4-methoxyphenyl)-3-(trifluoromethyl)-3H-diazirine in the presence of equimolar solutions of phenol and tyrosine derivatives leads to Friedel–Crafts alkylations (see scheme), which suggests a strategy for the development of “cleaner” diazirines for chemical biology.
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A short route to a partially aromatic version of the eunicellane skeleton, which occurs in cytostatic marine diterpenoids, was developed. The key step is the pinacol cyclization of a p-cymene-derived C20 keto aldehyde to form the 10-membered ring of the [8.4.0] bicycle. We observed different reactivities upon employment of the SmI2/THF or TiCl3/Zn–Cu/DME reagent system. Upon treatment with SmI2 in THF, the arylalkynes cyclized to novel [4.2.0] cyclohexylidene benzocyclobutanols, whereas the corresponding arylalkenes reacted to the desired [8.4.0] system. Under McMurry conditions, the alkynes afforded the [8.4.0] system, and this represents the first de novo synthesis of the complete eunicellane skeleton with a benzene partial structure.
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T. Wartmann, T. Lindel, "L-Phototryptophan", Eur. J. Org. Chem. 2013, 1649-1652.
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Phototryptophan is a new photoactivatable amino acid designed to be incorporated into tryptophan-containing peptides for photoaffinity labeling. The synthesis of phototryptophan starts from 6-bromoindole with the installation of an 1-azi-2,2,2-trifluoroethyl moiety, followed by microwave-assisted condensation with serine under mild conditions. Separation of the N-acetylated enantiomers was possible by employing Aspergillus aminoacylase. Differential scanning calorimetry showed that phototryptophan is thermally stable up to 100 °C. Boc-L-Phototryptophan was used to assemble a diazirine analog of the marine natural product hemiasterlin.
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