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

ABSTRACT: 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-?-D-ribofuranose as the starting material. The critical step was the SnCl4 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.

SUBMITTER: Ding H

PROVIDER: S-EPMC4142848 | biostudies-other | 2014

REPOSITORIES: biostudies-other

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

Ding Haixin H Li Wei W Ruan Zhizhong Z Yang Ruchun R Mao Zhijie Z Xiao Qiang Q Wu Jun J

Beilstein journal of organic chemistry 20140724

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 SnCl4 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. ...[more]

PMID: 25161727

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