Studies on nucleosidesⅤ: Total synthesis of diacetyl neosidomycin

Abstract

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.

Key words: NUCLEOSIDE, TOTAL SYNTHESIS, CATALYTIC HYDROGENATION

CLC Number:

R914

Cite this article

ZHANG JUNLIANG;CAI MENGSHEN. Studies on nucleosidesⅤ: Total synthesis of diacetyl neosidomycin[J]. Acta Chimica Sinica, 1996, 54(1): 84-89.

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核苷研究Ⅴ: 双乙酰赛吲哚毒素的全合成