Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 10, Issue -, Pages 1681-1685Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.10.176
Keywords
marine nucleosides; natural products; total synthesis; trachycladines A and B; Vorbruggen glycosylation
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Funding
- NSFC [20962009, 21062006]
- NCET [11-1000]
- Education Department of the Jiangxi Province [GJJ11223, GJJGJJ12583]
- Training Program of Jiangxi Youth Scientists
- Bureau of Science & Technology of Nanchang City
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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-beta-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.
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