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Efficient conversion of aucubin into 6-epi-aucubin
1Laboratoire de Pharmacognosie de l'Universite Rene Descartes-URA/CNRS 1310, Faculte des Sciences Pharmaceutiques et Biologiques, 4 avenue de l'Observatoire 75006 Paris, France.
Journal of Natural Products
|March 17, 1999
Summary
Researchers selectively deprotected peracetylaucubin to create 6-O-acetylaucubin. This intermediate was then converted to 6-epi-aucubin through benzoylation, inversion, and deprotection, yielding a key aucubin derivative.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Carbohydrate Chemistry
Background:
- Aucubin and its derivatives are iridoid glycosides with diverse biological activities.
- Efficient synthetic routes to aucubin analogs are crucial for structure-activity relationship studies.
- Selective functionalization of polyhydroxylated natural products presents synthetic challenges.
Purpose of the Study:
- To develop a synthetic strategy for accessing 6-epi-aucubin from peracetylaucubin.
- To explore selective deprotection and functionalization methods for aucubin derivatives.
- To achieve stereoselective inversion at a key position in the aucubin scaffold.
Main Methods:
- Selective deacetylation of peracetylaucubin using potassium cyanide (KCN).
- Benzoylation of the resulting intermediate to form a penta-O-benzoyl derivative.
- Stereochemical inversion via a modified Mitsunobu reaction followed by deprotection.
Main Results:
- Selective deprotection yielded 6-O-acetylaucubin.
- Conversion to 2',3',4',6',10-penta-O-benzoylaucubin was achieved.
- The Mitsunobu reaction successfully inverted the configuration, affording 6-epi-aucubin after deprotection.
Conclusions:
- A viable synthetic route to 6-epi-aucubin was established.
- Selective deprotection and Mitsunobu inversion are effective strategies for aucubin modification.
- The synthesized 6-epi-aucubin can serve as a valuable tool for further biological investigations.