First Total Synthesis of Marine Natural Nucleoside Kipukasin D

doi:10.6023/cjoc201806028

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3351-3355.DOI: 10.6023/cjoc201806028 Previous Articles Next Articles

Notes

海洋天然核苷Kipukasin D的首次全合成

丁海新^a, 李闯^a, 董祥有^a, 曹伴鹏^a, 张宁^b, 洪三国^b, 肖强^a

a 江西科技师范大学有机功能分子研究所江西省有机功能分子重点实验室南昌 330013;
b 南昌大学化学学院南昌 330031

收稿日期:2018-06-19 修回日期:2018-07-11 发布日期:2018-08-23
通讯作者: 肖强 E-mail:xiaoqiang@tsinghua.org.cn
基金资助:
国基自然科学基金（Nos.21462019，21676131）、江西省科技厅重点项目（No.20143ACB20012）和江西省教育厅科技（No.170673）资助项目.

First Total Synthesis of Marine Natural Nucleoside Kipukasin D

Ding Haixin^a, Li Chuang^a, Dong Xiangyou^a, Cao Banpen^a, Zhang Ning^b, Hong Sanguo^b, Xiao Qiang^a

a Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang 330013;
b Department of Chemistry, Nanchang University, Nanchang 330031

Received:2018-06-19 Revised:2018-07-11 Published:2018-08-23
Contact: 10.6023/cjoc201806028 E-mail:xiaoqiang@tsinghua.org.cn
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).

1. First Total Synthesis of Marine Natural Nucleoside Kipukasin D.PDF(1279KB)

Abstract

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

Cite this article

Ding Haixin, Li Chuang, Dong Xiangyou, Cao Banpen, Zhang Ning, Hong Sanguo, Xiao Qiang. First Total Synthesis of Marine Natural Nucleoside Kipukasin D[J]. Chin. J. Org. Chem., 2018, 38(12): 3351-3355.

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海洋天然核苷Kipukasin D的首次全合成

First Total Synthesis of Marine Natural Nucleoside Kipukasin D

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