3-O-去甲基孢子丝菌素A的全合成

Total synthesis of 3-O-demethylsporaricin A.

作者信息

Yasuda N, Matsuda K, Tsutsumi H, Takaya T

出版信息

J Antibiot (Tokyo). 1985 Nov;38(11):1512-25. doi: 10.7164/antibiotics.38.1512.

DOI:10.7164/antibiotics.38.1512

Abstract

The novel, semisynthetic pseudodisaccharide antibiotic, 3-O-demethylsporaricin A, was synthesized via 3-O-demethylsporaricin B obtained by glycosidation of its aminocyclitol part. The aminocyclitol part was synthesized as D,L-form from D,L-(1,2,3/4,5,6)-1,4-bis(benzyloxy-carbonylamino)-5,6-O-isopropyl idene-2,3,5,6-cyclohexanetetraol via three key steps, namely, deoxygenation, inversion of a hydroxyl group, and N-methylation. The physical and biological properties of synthetic 3-O-demethylsporaricin A and an authentic sample derived from sporaricin B were identical.

摘要

新型半合成假二糖抗生素3 - O - 去甲基sporaricin A是通过其氨基环醇部分糖苷化得到的3 - O - 去甲基sporaricin B合成的。氨基环醇部分由D,L-(1,2,3/4,5,6)-1,4 - 双(苄氧羰基氨基)-5,6 - O - 异丙叉基 - 2,3,5,6 - 环己烷四醇以D,L - 形式通过三个关键步骤合成，即脱氧、羟基构型翻转和N - 甲基化。合成的3 - O - 去甲基sporaricin A与源自sporaricin B的正品样品的物理和生物学性质相同。