Naranda A, Lopotar N, Kelnerić Z
PLIVA Research Institute, Zagreb, Croatia.
J Antibiot (Tokyo). 1997 Oct;50(10):860-5. doi: 10.7164/antibiotics.50.860.
Opening the oxirane ring of 12,13-epoxydesmycosin dimethylacetal (1) by catalytic hydrogenation gave the 10,11-dihydro-12,13-epoxy derivative (3) as the main product. Reductive oxirane cleavage was accomplished with dissolved metal (Zn) giving the 10,13-dihydro-13-hydroxy compound (6). Mild acid hydrolysis of 6 gave expected 10,13-dihydro-13-hydroxydesmycosin (8), but hydrolysis of 3, under the same conditions, gave three tautomeric desepoxy products.
通过催化氢化打开12,13 - 环氧去甲麦角甾醇二甲基缩醛（1）的环氧乙烷环，得到10,11 - 二氢 - 12,13 - 环氧衍生物（3）作为主要产物。用溶解金属（锌）实现环氧乙烷的还原裂解，得到10,13 - 二氢 - 13 - 羟基化合物（6）。6的温和酸水解得到预期的10,13 - 二氢 - 13 - 羟基去甲麦角甾醇（8），但在相同条件下3的水解得到三种互变异构的脱环氧产物。
