Marine drugs

First total synthesis of a naturally occurring iodinated 5′-deoxyxylofuranosyl marine nucleoside

J Sun, Y Dou, H Ding, R Yang, Q Sun, Q Xiao

文献索引：Sun, Jianyun; Dou, Yanhui; Ding, Haixin; Yang, Ruchun; Sun, Qi; Xiao, Qiang Marine Drugs, 2012 , vol. 10, # 4 p. 881 - 889

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被引用次数: 11

摘要

Abstract: 4-Amino-7-(5′-deoxy-β-D-xylofuranosyl)-5-iodo-pyrrolo [2, 3-d] pyrimidine 1, an unusual naturally occurring marine nucleoside isolated from an ascidan, Diplosoma sp., was synthesized from D-xylose in seven steps with 28% overall yield on 10 g scale. The key step was Vorbrüggen glycosylation of 5-iodo-pyrrolo [2, 3-d] pyrimidine with 5-deoxy-1, 2-O- diacetyl-3-O-benzoyl-D-xylofuranose. Its absolute configuration was confirmed.