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Title: | A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether | Authors: | Tee, J.T. Keane, T. Meijer, A.J.H.M. Khaledi, H. Rahman, N.A. Chee, C.F. |
Keywords: | Biomimetics Carbon Cyclization |
Issue Date: | 2016 | Journal: | Synthesis (Germany) Volume 48, Issue 14, 15 July 2016, Article number ss-2015-t0694-op, Pages 2263-2270 | Abstract: | A strategy toward the biomimetic synthesis of morusalbanol A pentamethyl ether is described. The synthesis is based on a hydrogen-bond-assisted Diels-Alder cycloaddition between a dehydroprenyl diene and a chalcone dienophile. Selective cleavage of the ortho-methyl ether of the resulting cycloadduct allows rotation of the C3-C21 bond and subsequent intramolecular cyclization affords the pentamethyl ether of (±)-morusalbanol A. As with the natural product, morusalbanol A, a number of key proton and carbon signals are absent in the NMR spectra of the title product. © Georg Thieme Verlag Stuttgart New York. | DOI: | 10.1055/s-0035-1560434 |
Appears in Collections: | COE Scholarly Publication |
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