A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether

A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether

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...

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Bibliographic Details
Main Authors: Tee, J.T., Keane, T., Meijer, A.J.H.M., Khaledi, H., Rahman, N.A., Chee, C.F.
Format: Article
Language:English
Published: 2017
Subjects:
Biomimetics
Carbon
Cyclization
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Institution: Universiti Tenaga Nasional
Language: English
Description
Summary: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.

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