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Original Articles

An efficient semi-synthesis and structure revision of a cytotoxic triterpenoid 25-acetoxy-3α-hydroxyolean-12-en-28-oic acid from Liquidamber styraciflua

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Pages 271-276 | Received 28 Jun 2007, Accepted 18 Oct 2007, Published online: 17 Aug 2009
 

Abstract

An efficient partial synthesis of 25-acetoxy-3α-hydroxyolean-12-en-28-oic acid (1), starting from oleanolic acid (2), has been developed in an efficient manner (13 steps, 21% yield), employing a photochemical reaction of nitrite 8 for the introduction of C-25 substituting group as the key step. Based on the comparison of its spectral data with those reported for compound 1 isolated from Liquidamber styraciflua, we found the structure in that paper was incorrectly assigned, and should be revised as 3α-acetoxy-25-hydroxyolean-12-en-28-oic acid (15).

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