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Chemistry of Natural Compounds

, Volume 55, Issue 4, pp 762–764 | Cite as

Formation of Oleanan-12-One Triterpenoid from Taraxerol Via Wagner-Meerwein/Pinacol Rearrangement

  • Phan Minh GiangEmail author
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Oleanane-type triterpenoids, both natural and semisynthetic, are reported to exhibit interesting biological or pharmacological properties such as anti-HIV (human immunodeficiency virus) and anticancer activities [1]. The major strategy in the semisynthesis of oleanane derivatives is transformations of functional groups on the pentacyclic oleanane skeleton [2]. The occurrence of C-12- or C-15-oxygenated oleananes has been little reported in the literature [3]. Taraxerane-type triterpenoids such as taraxerone can be converted to 15-hydroxyolean-12-enes through acid-catalyzed rearrangement of their 14,15-epoxy derivatives [4]. We report herein the rearrangement of taraxerol (1) in the presence of excessive MCPBA (m-chloroperoxybenzoic acid) to 3β,15-dihydroxyolean-12-ene [5] and novel 3β,15-dihydroxyoleanan-12-one. Since taraxerane triterpenoids are readily available from plants of the family Euphorbiaceae, this Wagner-Meerwein/pinacol-type approach is applicable for the preparation of...

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Faculty of ChemistryVNU University of Science, Vietnam National UniversityHanoiVietnam

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