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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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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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spelling my.uniten.dspace-34682017-10-27T01:56:49Z A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether Tee, J.T. Keane, T. Meijer, A.J.H.M. Khaledi, H. Rahman, N.A. Chee, C.F. Biomimetics Carbon Cyclization 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. 2017-10-27T00:35:16Z 2017-10-27T00:35:16Z 2016 Article 10.1055/s-0035-1560434 en Synthesis (Germany) Volume 48, Issue 14, 15 July 2016, Article number ss-2015-t0694-op, Pages 2263-2270
institution Universiti Tenaga Nasional
building UNITEN Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Tenaga Nasional
content_source UNITEN Institutional Repository
url_provider http://dspace.uniten.edu.my/
language English
topic Biomimetics
Carbon
Cyclization
spellingShingle Biomimetics
Carbon
Cyclization
Tee, J.T.
Keane, T.
Meijer, A.J.H.M.
Khaledi, H.
Rahman, N.A.
Chee, C.F.
A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether
description 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.
format Article
author Tee, J.T.
Keane, T.
Meijer, A.J.H.M.
Khaledi, H.
Rahman, N.A.
Chee, C.F.
author_facet Tee, J.T.
Keane, T.
Meijer, A.J.H.M.
Khaledi, H.
Rahman, N.A.
Chee, C.F.
author_sort Tee, J.T.
title A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether
title_short A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether
title_full A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether
title_fullStr A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether
title_full_unstemmed A Strategy toward the Biomimetic Synthesis of (±)-Morusalbanol A Pentamethyl Ether
title_sort strategy toward the biomimetic synthesis of (±)-morusalbanol a pentamethyl ether
publishDate 2017
_version_ 1644493541890588672
score 13.214268

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