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...
Saved in:
Main Authors: | , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
2017
|
Subjects: | |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
id |
my.uniten.dspace-3468 |
---|---|
record_format |
dspace |
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 |
13.222552 |