Published January 1, 2014 | Version v1
Journal article Open

Semisynthesis of Libiguin A and Its Analogues by Trans-Lactonization of Phragmalin

  • 1. Latvian Inst Organ Synth, LV-1006 Riga, Latvia
  • 2. Fdn Rakoto Ratsimamanga, Inst Malgache Rech Appl, Antananarivo 102, Madagascar
  • 3. Uppsala Univ, Dept Pharmaceut Biosci, SE-75124 Uppsala, Sweden

Description

Libiguins are limonoids with highly potent sexual activity enhancing effects, originally isolated from the Madagascarian Meliaceae species Neobeguea mahafalensis, where they exist in only minute quantities. Their low natural abundance has hampered mapping of their biological effects. Here we describe an approach to the semisynthesis of libiguin A and its close analogues 1-3 starting from phragmalin, which is a limonoid present in high amounts in a commercially cultivated Meliaceae species, Chukrasia tabularis, allowing the preparation of libiguins in appreciable quantities.

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