International Union of Pure and Applied Chemistry

The syntheses of lamellarins and isoindolobenzazepine alkaloids*

Somsak Ruchirawat^1,2,3, Thumnoon Mutarapat³, Poolsak Sahakitpichan¹, Vanida Bhavakul⁴, and Chulabhorn Mahidol¹1. Chulabhorn Research Institute, Bangkok 10210, Thailand
2. Programme on Research and Development of Synthetic Drugs
3. Department of Chemistry, Mahidol University, Bangkok 10400, Thailand
4. Department of Chemistry, Faculty of Science, King Mongkut’s University of Technology, Thonburi, Bangkok 10140, Thailand

Abstract: Lamellarins are a group of marine natural products which were isolated from the prosobranch mollusc Lemellaria sp and the ascidians. Some of these lamellarins exhibit interesting biological activities including cell division inhibition, cytotoxicity, and immunological activity. The synthesis of lamellarin G trimethyl ether (I) and other analogs will be presented.

Chilenine, isolated from the plants of Berberidaceae by Shamma et al., is the first representative of the isoidolobenzazepine alkaloids. Many synthetic routes to this class of alkaloids will be briefly reviewed and our approach to the synthesis of its analog, chilenamine (II) will be disclosed.

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