Efficient synthesis of a peculiar vicinal diamine semiochemical from Streptomyces natalensis.
The pimaricin-inducing (PI) factor, produced by Streptomyces natalensis is a proposed pheromone with a peculiar vicinal diamine structure. The first synthesis of this molecule is reported. It features oxidative dimerization of an aci-nitro anion derived from tris(hydroxymethyl)nitromethane and disproportionation catalyst-facilitated hydrogenation of the resulting vicinal tertiary dinitro compound. As the synthesis requires only four steps with no chromatographic separations, it provides a convenient route to prepare PI factor for biological studies and industrial applications.
Morin
Jesse B
JB
Department of Chemistry, Brown University, 324 Brook Street, Providence, Rhode Island 02912, USA.
Sello
Jason K
JK
D002384:Catalysis; D003959:Diamines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010866:Natamycin / Q000302:isolation & purification* / Q000378:metabolism; D013302:Streptomyces / Q000737:chemistry*
D003959:Diamines; D010866:Natamycin