54 Asukamycinの化学構造

概要

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Structural studies on Asukamycin, an antibiotic produced by Streptomyces nodosus subsp. asukaensis, were undertaken by degradative as well as spectroscopic experiments including (a) acetolysis yielding 2-acetamido-1,3-cyclopentandione 3, (b) chromic acid oxidation giving an epoxybenzoquinone derivative 4, (c) formation of cyclohexanecarboxylic acid by nitric acid oxidation, (d) determination of the location of a tertiary carbinol group by the ^<13>C-{^1H}-NOE experiments, (e) stereochemical studies by the 270 MHz ^1H-nmr spectroscopy, and (f) deduction of the absolute configuration of the tertiary carbinol by the exciton chirality method, to assign the structure 1 for the antibiotic. Interestingly 1 contains a naturally quite rare monosubstituted cyclohexane group. Significant is that the stereochemistry of the tertiary carbinol group in the central C_7N unit turned out to be identical with that of 3-dehydro-quinic acid, which is a conceivable biosynthetic precursor. These chemical studies as well as the biosynthetic features will be discussed.
天然有機化合物討論会の論文
1979-09-20