Concise total synthesis of two marine natural nucleosides: trachycladines A and B

We report the first total synthesis of trachycladines A (10 steps, 34.2% overall yield) and B (11 steps, 35.0% overall yield) by using 5-deoxy-1,2,3-tri-O-acetyl-β-D-ribofuranose as the starting material. The critical step was the SnCl(4) assisted regio- and steroselective deprotection of perbenzyla...

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Detalles Bibliográficos
Autores principales: Ding, Haixin, Li, Wei, Ruan, Zhizhong, Yang, Ruchun, Mao, Zhijie, Xiao, Qiang, Wu, Jun
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4142848/
https://www.ncbi.nlm.nih.gov/pubmed/25161727
http://dx.doi.org/10.3762/bjoc.10.176
Descripción
Sumario:We report the first total synthesis of trachycladines A (10 steps, 34.2% overall yield) and B (11 steps, 35.0% overall yield) by using 5-deoxy-1,2,3-tri-O-acetyl-β-D-ribofuranose as the starting material. The critical step was the SnCl(4) assisted regio- and steroselective deprotection of perbenzylated 1-O-methyl-5-deoxyribofuranose. The enzyme adenylate deaminase (EC 3.5.4.6) was successfully applied to the chemoenzymatic synthesis of trachycladines B.

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