Four representative Δ-ginsenosides, namely, ginsenosides Rh (1), (20E)-Rh (2), Rg (3), and Rk (4) from Panax Ginseng, were chemically synthesized for the first time. Dehydration of the naturally occurring 20(S)-protopanaxatriol and 20(S)-protopanaxadiol provided all types of Δ-sapogenins, which were separated due to a judicious choice of protecting groups. The Δ-sapogenins were then directly glycosylated with glycosyl ortho-alkynylbenzoate donors under the catalysis of PhPAuNTf as key steps. The neutral conditions of the glycosylations were crucial to prevent the acid-labile Δ double bond from isomerization.
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| http://dx.doi.org/10.1021/acs.joc.7b02987 | DOI Listing |
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