Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
Org Biomol Chem. 2014 Jan 7;12(1):53-6. doi: 10.1039/c3ob42017e. Epub 2013 Nov 11.
The stereocontrolled synthesis of a racemic carboxylic acid of crambescin B, a marine alkaloid, is described. The synthesis features two highly stereoselective reactions: (I) palladium-catalyzed hydroxymethylation of an alkynyl aziridine having an N-guanidino group and (II) cascade bromocyclization providing a spiro-hemiaminal structure. The cell-based colorimetric assay showed that the synthesized carboxylic acid exhibited a potent inhibitory activity on voltage-gated sodium channels.
本文描述了海鞘生物碱 crambescin B 的外消旋羧酸的立体控制合成。该合成具有两个高度立体选择性的反应：（i）具有 N-胍基的炔基氮丙啶的钯催化羟甲基化和（ii）级联溴环化提供螺-半缩醛结构。基于细胞的比色测定表明，合成的羧酸对电压门控钠离子通道表现出很强的抑制活性。
