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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
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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