72 Tomaymycinおよびその類縁体の合成
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Tomaymycin is an antitumor antibiotic isolated from Streptomyces achromogenes. Tomaymycin and its Z-isomer were synthesized from L-hydroxyproline (3) and vanillin (9), as shown in Chart 1. Tomaymycin analogs were synthesized in a similar manner. On the basis of PMR and C-13 NMR spectra, the structure of Tomaymycin was determined as (2E,11R,11aS)-2-ethylidene-5,10,11,11a-tetrahydro-8-hydroxy-7,11-dimethoxy-5-oxo-1H-pyrrolo-(2,1-C)(1,4)-benzodiazepin. The absolute configuration at C_<11> was determined to be R-configuration by no coupling between H_<11> and H_<11a> in PMR spectrum. The E-configuration of the 2-ethylidene was determined by the high field shift of the adjacent methylene group which was shielded with the methyl group of the 2-ethylidene in C-13 NMR. L-Hydroxyproline (3) was converted to alkylidene derivatives (25-28) and oxime derivatives (23,24) via ketones (21,22) in order to synthesize Tomaymycin analogs, as shown in Chart 2. Tomaymycin analogs predicted antitumor activity and antibiotic activity.
- 天然有機化合物討論会の論文
- 1981-09-10
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