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
2004.0

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.

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