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

1

Issued Date

2004-02-06

Resource Type

Article

ISSN

14337851

DOI

10.1002/anie.200352043

Other identifier(s)

2-s2.0-4544263266

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Angewandte Chemie - International Edition. Vol.43, No.7 (2004), 866-868

Suggested Citation

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. Angewandte Chemie - International Edition. Vol.43, No.7 (2004), 866-868. doi:10.1002/anie.200352043 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/21259

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Title

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

Author(s)

Poonsakdi Ploypradith
 Chulabhorn Mahidol
 Poolsak Sahakitpichan
 Siriporn Wongbundit
 Somsak Ruchirawat

Other Contributor(s)

Chulabhorn Research Institute
 The Institute of Science and Technology for Research and Development, Mahidol University
 Mahidol University

Abstract

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.

Keyword(s)

Chemical Engineering
 Chemistry

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URI

https://repository.li.mahidol.ac.th/handle/123456789/21259

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Scopus 2001-2005