A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes

A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes

Alkaloid achievement: Lamellarins, a new class of potential nontoxic inhibitors of HIV-1 integrase that are also responsible for multidrug-resistance reversal in cancer cell lines, could be synthesized in three chemical steps and in 60% overall yields from two simple starting materials (see scheme)....

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Main Authors: Poonsakdi Ploypradith, Chulabhorn Mahidol, Poolsak Sahakitpichan, Siriporn Wongbundit, Somsak Ruchirawat
Other Authors: Chulabhorn Research Institute
Format: Article
Published: 2018
Subjects:
Chemical Engineering
Chemistry
Online Access:https://repository.li.mahidol.ac.th/handle/123456789/21259
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spelling th-mahidol.212592018-07-24T10:40:29Z A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes Poonsakdi Ploypradith Chulabhorn Mahidol Poolsak Sahakitpichan Siriporn Wongbundit Somsak Ruchirawat Chulabhorn Research Institute The Institute of Science and Technology for Research and Development, Mahidol University Mahidol University Chemical Engineering Chemistry Alkaloid achievement: Lamellarins, a new class of potential nontoxic inhibitors of HIV-1 integrase that are also responsible for multidrug-resistance reversal in cancer cell lines, could be synthesized in three chemical steps and in 60% overall yields from two simple starting materials (see scheme). The key step in the convergent synthetic approach involved the novel Michael addition/ring-closure reaction to give the pyrrole core and the ester group required for subsequent lactonization in one step. 2018-07-24T03:39:31Z 2018-07-24T03:39:31Z 2004-02-06 Article Angewandte Chemie - International Edition. Vol.43, No.7 (2004), 866-868 10.1002/anie.200352043 14337851 2-s2.0-4544263266 https://repository.li.mahidol.ac.th/handle/123456789/21259 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=4544263266&origin=inward
institution Mahidol University
building Mahidol University Library
continent Asia
country Thailand
Thailand
content_provider Mahidol University Library
collection Mahidol University Institutional Repository
topic Chemical Engineering
Chemistry
spellingShingle Chemical Engineering
Chemistry
Poonsakdi Ploypradith
Chulabhorn Mahidol
Poolsak Sahakitpichan
Siriporn Wongbundit
Somsak Ruchirawat
A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes
description Alkaloid achievement: Lamellarins, a new class of potential nontoxic inhibitors of HIV-1 integrase that are also responsible for multidrug-resistance reversal in cancer cell lines, could be synthesized in three chemical steps and in 60% overall yields from two simple starting materials (see scheme). The key step in the convergent synthetic approach involved the novel Michael addition/ring-closure reaction to give the pyrrole core and the ester group required for subsequent lactonization in one step.
author2 Chulabhorn Research Institute
author_facet Chulabhorn Research Institute
Poonsakdi Ploypradith
Chulabhorn Mahidol
Poolsak Sahakitpichan
Siriporn Wongbundit
Somsak Ruchirawat
format Article
author Poonsakdi Ploypradith
Chulabhorn Mahidol
Poolsak Sahakitpichan
Siriporn Wongbundit
Somsak Ruchirawat
author_sort Poonsakdi Ploypradith
title A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes
title_short A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes
title_full A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes
title_fullStr A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes
title_full_unstemmed A highly efficient synthesis of lamellarins K and L by the Michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes
title_sort highly efficient synthesis of lamellarins k and l by the michael addition/ring-closure reaction of benzyldihydroisoquinoline derivatives with ethoxycarbonyl-β-nitrostyrenes
publishDate 2018
url https://repository.li.mahidol.ac.th/handle/123456789/21259
_version_ 1763492891388280832

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