Development of Enantioselective Synthetic Routes to (−)-Kinamycin F and (−)-Lomaiviticin Aglycon

Identification of Alp1U and Lom6 as epoxy hydrolases and implications for kinamycin and lomaiviticin biosynthesis

The naturally occurring diazobenzofluorenes, kinamycins, fluostatins and lomaiviticins, possess highly oxygenated A-rings, via which the last forms a dimeric pharmacophore. However, neither the A-ring transformation nor the dimerization mechanisms have been explored thus far. Here we propose a unified biosynthetic logic for the three types of antibiotics and verify one key reaction via detailed...

Enantioselective synthesis of the lomaiviticin aglycon full carbon skeleton reveals remarkable remote substituent effects during the dimerization event.

Enantioselective Synthesis of the Elaiophylin Aglycon.

Elaiophylin (1) was isolated in 1959 by Arcamone and co-workers from cultures of Streptomyces melanosporus.1 Subsequently, this natural product has also been obtained from other strains of Streptomyces.2 Structure elucidation of 1, including assignment of absolute stereochemistry, was based on chemical degradation,3 NMR studies,4 and ultimately X-ray crystallographic analysis.5 Isolation and ch...

New products related to kinamycin from Streptomyces murayamaensis. II. Structures of pre-kinamycin, keto-anhydrokinamycin, and kinamycins E and F.

Four new colored components of Streptomyces murayamaensis sp. nov. Hata et Ohtani, the producer of the kinamycins, have been isolated and their structures determined by a combination of mass spectral, high field NMR and biosynthetic techniques. The first compound with the benz[b]carbazole skeleton in the biosynthetic pathway of kinamycin D has been named "pre-kinamycin" (7). A keto-epoxide kina...

Synthetic routes to new physics

metals individually: it does not matter too much what the other electrons are doing. Technically, if the behaviour of one electron is essentially independent of the others, one says that the electrons are ‘uncorrelated’. In contrast, an accurate description of electronic correlations in molecules is often essential if one is to make usefully accurate predictions. However, electronic correlation...