Chinese Journal of Organic Chemistry >
First Total Synthesis of Marine Natural Nucleoside Kipukasin D
Received date: 2018-06-19
Revised date: 2018-07-11
Online published: 2018-08-23
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21462019, 21676131), the Bureau of Science & Technology of Jiangxi Province (No. 20143ACB20012) and the Education Department of Jiangxi Province (No. 170673).
The first total synthesis of marine natural nucleoside kipukasin D was disclosed in 9 steps and 15.7% overall yield using commercially available tetra-O-acetyl-β-D-ribose as starting material. In Vorbrüggen glycosylation, ortho-iodinebenzoate acted as neighboring participating group leading to β-nucleoside. The key step was selectively deprotection of 2'-O and 5'-O ortho-alkynylbenzoates by freshing prepared Ph3PAuOTFA in the presence of ethanol (6 equiv.) and H2O (1 equiv.) in dichloromethane (DCM). The reaction condition of our newly developed approach is very mild and neutral, which effectively avoids the transesterification between 2'-OH and 3'-OH. The result further demonstrat that ortho-alkynylbenzoate is an orthogonal protecting group compatible with other ester groups, which could find wide applications in nucleoside and carbohydrate chemistry.
Key words： nucleoside; neighboring-group; transesterification; catalysis; total synthesis
Ding Haixin , Li Chuang , Dong Xiangyou , Cao Banpen , Zhang Ning , Hong Sanguo , Xiao Qiang . First Total Synthesis of Marine Natural Nucleoside Kipukasin D[J]. Chinese Journal of Organic Chemistry, 2018 , 38(12) : 3351 -3355 . DOI: 10.6023/cjoc201806028
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