Semisynthesis of libiguin A and its analogues by trans-lactonization of phragmalin.
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.
Latvian Institute of Organic Synthesis , Aizkraukles 21, Riga LV-1006, Latvia.
Liene
L
Grigorjeva
Edvards
E
Liepinsh
Solofoniaina
S
Razafimahefa
Aleh
A
Yahorau
Sviatlana
S
Yahorava
Philippe
P
Rasoanaivo
Aigars
A
Jirgensons
Jarl E S
JE
Wikberg
D036701:Limonins / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D029582:Meliaceae / Q000737:chemistry; D008968:Molecular Conformation
D036701:Limonins; C000592852:libiguin A; C000593079:phragmalin