核苷研究Ⅴ: 双乙酰赛吲哚毒素的全合成

赛吲哚霉素的双乙酰衍生物已由吲哚曼 -吲哚法合成。吲哚-3-乙酸经催化氢化, 甲酯化和氨解反应得到吲哚曼-3-乙酰胺(9); 将4-去氧-D-核-吡喃己糖以三苯甲基保护后乙酰化。消除保护基再经氧化和甲酯化等反应, 得到1,2,3-O-三乙酰基-4-去氧-β-D-核-吡喃己糖醛酸甲酯(6), 将化合物6和9先缩合后脱氢即得到赛吲哚霉素的双乙酰衍生物2。赛吲哚霉素的类似物1-(3-氨羰甲基吲哚基)-2,3,4,6-O-四乙酰基-β-D-吡喃葡萄糖苷(13)也由相似的方法合成。

Studies on nucleosidesⅤ: Total synthesis of diacetyl neosidomycin

The diacetate of neosidomycin had been synthesized by indoline- indole method. Firstly, indoline-3-acetamide (9) was prepared from indole-3-acetic acid by catalytic hydrogenation, esterification and aminolysis. And then methyl 1,2,3, -O-triacetyl-4-deoxy-β-D-ribo- hexopyranuronate (6) was synthesized from 4-deoxy-D-ribo-hexopyranose (3) through triphenylmethylation, acetylation, detriphenylmethylation. oxidation and esterification. The indoline-N-glycoside 10 was obtained by the condensation of 9 and 6. Finally, the diacetate of neosidomycin 2 (methyl 1-(3-carbamoylmethylindoyl)-2,3-O-diacetyl-4-deoxy-D-ribo- hexopyranoside] uronate], was prepared by the dehydrogenation of 10 with DDQ. With the similar method 1-(3-carbamoylmethylindoyl)-2,3,4,6- O-tetraacetyl-β-D-glucopyranoside (13) was synthesized.