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First total synthesis of kipukasin A.

ABSTRACT: In this paper, a practical approach for the total synthesis of kipukasin A is presented with 22% overall yield by using tetra-O-acetyl-?-D-ribose as starting material. An improved iodine-promoted acetonide-forming reaction was developed to access 1,2-O-isopropylidene-?-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 % Ph₃PAuOTf in dichloromethane to provide kipukasin A in high yield and regioselectivity.

SUBMITTER: Li C

PROVIDER: S-EPMC5433220 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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First total synthesis of kipukasin A.

Li Chuang C Ding Haixin H Ruan Zhizhong Z Zhou Yirong Y Xiao Qiang Q

Beilstein journal of organic chemistry 20170509

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 p ...[more]

PMID: 28546843

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