Synthesis of 4,9-dimethyldecanoic acid

ORGN 542

Ariel O. Otero-Rodriguez, arielo.otero@gmail.com and Mayra Pagán, mayrapaganortiz@yahoo.com. Departamento de Química, Universidad de Puerto Rico en Cayey, Avenida Antonio R. Barceló, Cayey, PR 00736
Methyl-branched fatty acids are commonly found in bacteria.(1) Several of these branched short-chain fatty acids have been reported to have antitumor or antimicrobial activity.(2) The 4,9-dimethyldecanoic acid was isolated for the first time in nature from the halophilic bacterium Bacillus sp. from the salt pans of Burgas in Bulgaria.(3)

A synthetic scheme to obtain 4,9-dimethyldecanoic acid was developed to provide enough material to perform bioassays in order to assess possible biological activities. The 4,9-dimethyldecanoic acid will be obtain as a single enantiomer, since the synthesis starts with a chiral starting material. The advances in this synthesis will be presented.

(1) Chou, S.; Chedore, P.; Haddad, A.; Paul, N. R.; Kasatiya, S. J. Clin. Microbiol. 1996, 34, 1317-1320.

(2) Adamczeski, M.; Reed, A. R.; Crews, P. J. Nat. Prod. 1995, 58, 201-208.

(3) Carballeira, N. M.; Miranda, C.; Lozano, C. M.; Nechev, J. T.; Ivanova, A.; Stefanov, K.; Ilieva, M.; Tzvetkova, I. J. Nat. Prod. 2001; 64, 256.