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First total synthesis of kipukasin A (2017)

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

Beilstein-Institut

In: Beilstein Journal of Organic Chemistry

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Publication Date: 2017-05-10

Description: In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra- O -acetyl-β-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2- O -isopropylidene-α-D-ribofuranose. For the first time, ortho- alkynylbenzoate was used as protecting group for the 5-hydoxy group. After subsequent Vorbrüggen glycosylation, the protecting group could be removed smoothly in the presence of 5 mol % Ph 3 PAuOTf in dichloromethane to provide kipukasin A in high yield and regioselectivity. Beilstein J. Org. Chem. 2017, 13, 855–862. doi:10.3762/bjoc.13.86

Keywords: gold catalysiskipukasin Amarine nucleosidetotal synthesisVorbrüggen glycosylation

Electronic ISSN: 1860-5397

Topics: Chemistry and Pharmacology

Published by Beilstein-Institut

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