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Synthesis of Ocotillol-Type Ginsenosides
Renzeng Shen1, Xin Cao1, Stephane Laval1
1State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
The Journal of Organic Chemistry
|July 12, 2016
Summary
This study presents a novel gold(I)-catalyzed synthesis of 14 ocotillol-type ginsenosides. The method efficiently glycosylates sapogenin derivatives, yielding various mono- and di-glycosylated compounds.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Ginsenosides are key bioactive compounds found in Panax species.
- Ocotillol-type ginsenosides possess unique pharmacological properties.
- Efficient synthesis of these complex molecules remains a challenge.
Purpose of the Study:
- To develop a convenient and efficient synthetic route for ocotillol-type ginsenosides.
- To explore the regioselectivity of glycosylation on ocotillol sapogenin derivatives.
- To synthesize a library of mono- and di-glycosylated ocotillol derivatives.
Main Methods:
- Gold(I)-catalyzed glycosylation of ocotillol sapogenin derivatives.
- Utilized glucosyl ortho-alkynylbenzoate donors.
- Employed a rational protecting group strategy.
- Investigated regioselectivity for 3,25-diol sapogenins.
Main Results:
- Successfully synthesized 14 ocotillol-type ginsenosides.
- Achieved regioselective glycosylation at the tertiary 25-OH position.
- Prepared mono 3-O-glucosyl, 6-O-glucosyl, 25-O-glucosyl, and 3,25-di-O-glucosyl derivatives.
- Synthesized compounds with both R and S configurations at C-24.
Conclusions:
- The gold(I)-catalyzed glycosylation is an effective method for synthesizing ocotillol-type ginsenosides.
- The developed strategy allows for controlled synthesis of specific glycosylation patterns.
- This work provides access to diverse ginsenoside analogs for further biological evaluation.
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