First total synthesis of kipukasin A
2017 ◽
Vol 13
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pp. 855-862
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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 % Ph3PAuOTf in dichloromethane to provide kipukasin A in high yield and regioselectivity.
2013 ◽
Vol 8
(6)
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pp. 1934578X1300800
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1983 ◽
Vol 61
(10)
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pp. 2442-2444
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2019 ◽
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