Scientists from the ZIOC have proposed an effective method for obtaining lamellarins

Lamellarins are a family of polycyclic alkaloids isolated from various marine organisms. These compounds exhibit high antitumor activity and also successfully inhibit HIV-1 integrase. Due to the promising biological properties of lamellarins and the limited natural sources, the development of methods for their chemical synthesis is extremely important.

Scientists from the Laboratory of Medicinal Chemistry of the ZIOC proposed a simple and effective way to obtain a lamellarin framework. The method is based on a 1,3-dipolar cycloaddition reaction between isoquinoline ylides and nitrostilbenes, leading to the formation of 1,2-diarylpyrrolo[2,1-a]isoquinoline-3-carboxylates. As a result of the subsequent O-demethylation of the obtained compounds, lamellarin structures are formed. The developed approach does not require expensive or difficult-to-prepare starting compounds and makes it possible to obtain a wide range of lamellarins in good yields.

Source:

E. A. Silyanova, A. V. Samet, V. V. Semenov A Two-Step Approach to a Hexacyclic Lamellarin Core via 1,3-Dipolar Cycloaddition of Isoquinolinium Ylides to Nitrostilbenes J. Org. Chem. 2022, 87, 6444−6453. DOI: 10.1021/acs.joc.2c00312.