An unprecedented gedunin rearrangement reaction converts a methyl group into the methylene group of a cyclopropyl ring |
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| Authors: | Samuel E. Okhale John Decatur Yasuhiro Itagaki Joseph O. Amupitan George I. Ndukwe George Ellestad Joseph I. Okogun |
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| Affiliation: | 1. Department of Medicinal Plant Research and Traditional Medicine, National Institute for Pharmaceutical Research and Development, Idu Industrial Area, P.M.B. 21 Garki, Abuja, Nigeria;2. Department of Chemistry, Columbia University, USA;3. Department of Chemistry, Ahmadu Bello University, Zaria, Nigeria;4. Pax Herbal Clinic & Research Laboratories, Benedictine Monastery, PO Box 150, Ewu-Esan, Edo State, Nigeria;5. Department of Chemistry, University of Ibadan, Ibadan, Nigeria |
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| Abstract: | Herein we describe an unprecedented formation of a cyclopropane ring through the conversion of a methyl group that was not functionalized for the purpose. In a one-step reaction, 7-deacetoxy-7α-hydroxygedunin (4) afforded two new gedunin derivatives, namely 7-deacetoxy-13,14,18-cyclopropyl-7α,15β, 17ξ-trihydroxy-gedu-16-oic acid (7) and 7-deacetoxy-9,11-en-7α,15β-dihydroxygedunin (8) along with the known 7-deacetoxy-7,9-diene-15β-hydroxygedunin (5). |
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| Keywords: | Gedunin Acid-catalysed rearrangement reaction Intramolecular cyclopropanation Chemosystematics Phylogenetic history |
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