Lavendamycin

Dark red crystals

> 300 ° C

Template: Infobox chemical / molecular formula search available

Lavendamycin is a naturally occurring chemical compound, which may be isolated from the fermentation broth of the soil bacterium Streptomyces lavendulae. It has antibiotic properties and significant anti-proliferative effects against several cancer cell lines. However, the use of Lavendamycin as a cytostatic agent in cancer therapy failed because of the poor water solubility and non-specific cytotoxicity of the compound.

Discovery

Lavendamycin was the first time in 1981 by Doyle et al. isolated from Streptomyces lavendulae. As a crystallization of the compound was not possible a direct elucidation of the molecular structure by X-ray analysis was not possible. By careful analysis by NMR, IR, UV / VIS spectroscopy and mass spectrometry of the compound were the pentacyclic structure consisting are assigned from a β - carboline and Chinolinchinon unit.

Total syntheses

Its attractive biological properties and its complex structure Lavendamycin made ​​the target of numerous total syntheses. A few years after the structure assignment by Doyle et al. were able to develop this natural product research groups of Kende, Hibino, Rao and Boger independently total syntheses. The discovery that analogs of Lavendamycins are potent inhibitors of HIV reverse transcriptase, led to develop numerous other trials efficient access to Lavendamycin in the 90s. Many reaction steps, low overall yields ( 0.5-2 %) or poorly available starting materials make these syntheses, however unattractive for a systematic development of Lavendamycin. These therefore are the total syntheses of Behforouz and nits that allow a flexible structure of Lavendamycin scaffold in high yields.