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
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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/20.500.14594/21259
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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). 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.
