First total synthesis of kipukasin A

• Chuang Li,
• Haixin Ding,
• Zhizhong Ruan,
• Yirong Zhou and
• Qiang Xiao

Beilstein J. Org. Chem. 2017, 13, 855–862, doi:10.3762/bjoc.13.86

• Chuang Li Haixin Ding Zhizhong Ruan Yirong Zhou Qiang Xiao Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science & Technology Normal University, Nanchang, Jiangxi 330013, China 10.3762/bjoc.13.86 Abstract In this paper, a practical approach for the total synthesis of kipukasin A is

• subsequent Vorbrüggen 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. Keywords: gold catalysis; kipukasin A; marine nucleoside; total synthesis; Vorbrüggen glycosylation

• group at 2’-OH position. To the best of our knowledge, they are the first naturally occurring aroyl nucleosides reported up to now. The biological assays showed that kipukasin A owned modest activity against Gram-positive bacteria Staphylococcus aureus (ATCC 29213) [11]. During our ongoing biological