First total synthesis of kipukasin A

被引：5

作者：

Li, Chuang ^{[1
]}

Ding, Haixin ^{[1
]}

Ruan, Zhizhong ^{[1
]}

Zhou, Yirong ^{[1
]}

Xiao, Qiang ^{[1
]}

机构：

[1] Jiangxi Sci & Technol Normal Univ, Jiangxi Key Lab Organ Chem, Nanchang 330013, Jiangxi, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 13卷

基金：

美国国家科学基金会;

关键词：

gold catalysis; kipukasin A; marine nucleoside; total synthesis; Vorbruggen glycosylation; MARINE NATURAL-PRODUCTS; ASPERGILLUS-VERSICOLOR; NUCLEOSIDE DERIVATIVES; GENERAL-SYNTHESIS; ANALOGS; AGENTS; GLUCURONIDES; INHIBITION; MIGRATION; EFFICIENT;

D O I：

10.3762/bjoc.13.86

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-beta-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-isopropylidene-alpha-D-ribofuranose. For the first time, ortho-alkynylbenzoate was used as protecting group for the 5-hydoxy group. After subsequent Vorbruggen glycosylation, the protecting group could be removed smoothly in the presence of 5 mol % Ph3PAuOTf in dichloromethane to provide kipukasin A in high yield and regioselectivity.

引用

页码：855 / 862

页数：8

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