623154-25-6Relevant academic research and scientific papers
The first total synthesis of the marine fatty acid (±)-9-methoxypentadecanoic acid: A synthetic route towards mid-chain methoxylated fatty acids
Carballeira, Nestor M.,Miranda, Carlos
, p. 63 - 67 (2003)
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.
Enantioselective synthesis of (+)-patulolide C via proline-catalyzed sequential α-aminooxylation and Horner-Wadsworth-Emmons olefination
Sabitha, Gowravaram,Chandrashekhar,Yadagiri,Yadav
scheme or table, p. 3824 - 3826 (2010/08/19)
The enantioselective total synthesis of (+)-patulolide C isolated from Penicillium urticae has been achieved from commercially available 9-decen-1-ol. Jacobsen's kinetic resolution and sequential a-aminooxylation and Horner-Wadsworth-Emmons (HWE) olefinat
Ring-conformer effects of the cyclopropyl group: First use of trans-(2r,3r)-cyclopropanecarbaldehydes as electrophiles in diastereoselective baylisihillman reaction
Krishna, Palakodety Radha,Kishore,Reddy, P. Srinivas
scheme or table, p. 2605 - 2608 (2010/03/03)
trans-(2R,3R)-Cyclopropanecarbaldehydes are used as novel electrophiles in the Baylis-Hillman reaction to afford adducts in good yields (75-85%) and diastereoselectivities (60-90%).
