1 デストマイシンCの合成

概要

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Destomycin C, a pseudo-trisaccaride antibiotic having an interglycosidic spiro-orthoester linkage, was synthesized. Stereoselective formation of orthoester linkage in the previously developed method, where glyconolactone and diol were coupled in the presence of TMSOTf, was studied using various derivatives of the diol, and achieved by the reaction of the diols having monosilyl or two different silyl groups. Anomerization of β-mannopyranoside was observed on the formation of orthoester in CH_2Cl_2 but depressed in ether. The total synthesis of destomycin C was performed in the following sequence: (1) formation of β-glycosidic linkage between D-mannopyranose and deoxystreptamine derivatives, (2) 2',3'-O-glycosylidenation of the pseudo-disaccharide with destomic acid derivative, which was derived from destomycin A, (3) inversion of configuration at C-4 of the mannopyranosyl moiety and (4) deprotection. Synthetic compound was proved to be identical with natural destomycin C by comparison of ^1H-NMR spectra at 500 MHz.
天然有機化合物討論会の論文
1985-09-07