359701-60-3Relevant academic research and scientific papers
Regio- and stereoselective hydroxylation of 10-undecenoic acid with a light-driven P450 BM3 biocatalyst yielding a valuable synthon for natural product synthesis
Kato, Mallory,Nguyen, Daniel,Gonzalez, Melissa,Cortez, Alejandro,Mullen, Sarah E.,Cheruzel, Lionel E.
, p. 5687 - 5691 (2014)
We report herein the selective hydroxylation of 10-undecenoic acid with a light-activated hybrid P450 BM3 enzyme. Under previously developed photocatalytic reaction conditions, only a monohydroxylated product is detected by gas chromatography. Hydroxylation occurs exclusively at the allylic position as confirmed from a synthesized authentic standard. Investigation into the stereochemistry of the reaction indicates that the R enantiomer is obtained in 85% ee. The (R)-9-hydroxy-10-undecenoic acid obtained enzymatically is a valuable synthon en route to various natural products further expanding the light-activated P450 BM3 biocatalysis and highlighting the advantages over traditional methods.
A concise synthesis of pinellic acid using a cross-metathesis approach
Miura, Ayako,Kuwahara, Shigefumi
experimental part, p. 3364 - 3368 (2009/09/06)
A new enantioselective synthesis of pinellic acid, a trihydroxy unsaturated fatty acid exhibiting oral adjuvant activity for nasally administered influenza vaccine, has been accomplished using a cross-metathesis reaction between two terminal olefin interm
