The first total synthesis of the marine fatty acid (+/-)-9-methoxypentadecanoic acid: a synthetic route towards mid-chain methoxylated fatty acids.
The marine fatty acid (+/-)-9-methoxypentadecanoic acid was synthesized for the first time in seven steps (7.8% overall yield) starting from commercially available 9-decen-1-ol. The key step in the synthesis was the coupling of pentylmagnesium bromide with 1-benzyloxy-9,10-epoxydecane under 1,5-cyclooctadiene copper (I) chloride catalysis. Nuclear magnetic resonance data are provided for the first time for this type of methoxylated fatty acids and the synthetic approach utilized is of general applicability since it can be used in the synthesis of other mid-chain methoxylated fatty acids. This synthetic methodology should afford sufficient quantities of these fatty acids for biological evaluation. The spectral data obtained for the title compound will also be helpful in subsequent characterizations of other mid-chain methoxylated fatty acids using nuclear magnetic resonance spectroscopy.
Carballeira
Néstor M
NM
Department of Chemistry, University of Puerto Rico, P.O. Box 23346, San Juan 00931-3346, Puerto Rico. ncarball@upracd.upr.clu.edu
Miranda
Carlos
C
D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005233:Fatty Alcohols / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D000461:Rhodophyta / Q000737:chemistry; D013237:Stereoisomerism
D005227:Fatty Acids; D005233:Fatty Alcohols; C117025:pentadecanoic acid