Chevalley, Alice published the artcileModel Studies for a Ring-Closing Metathesis Approach to the Bafilomycin Macrolactone Core from a 2,2-Dimethoxy Tetraenic Ester Precursor, Name: Allyldiphenylphosphine oxide, the publication is European Journal of Organic Chemistry (2013), 2013(36), 8265-8278, database is CAplus.
A ring-closing metathesis strategy is reported for the construction of the 16-membered macrolactone core of bafilomycin. One decisive key feature is the presence of a 2,2-dimethoxy-ketal functionality at C-2 that provides the required flexibility to the tetraene acid ester precursor, allowing the ring-closing metathesis reaction to take place. Three different model esters of increasing complexity were successfully subjected to the 1,3-diene-ene ring-closing metathesis reaction. The best promoter for the simplest esters was the Grubbs first-generation pre-catalyst. A Hoveyda-Grubbs-type trifluoroacetamide-containing pre-catalyst developed by Mauduit’s group gave satisfactory results for the most complex ester. In all experiments, the (12Z)-configured isomer was obtained as the major product. Subsequent microwave-promoted methanol elimination was achieved on the simplest model compound using camphorsulfonic acid (CSA) as a catalyst. Under these conditions, a (E/Z)-isomerization of the double bond at C-4, as well as ca. 50% isomerization of the (12Z)-double bond into the corresponding (12E)-isomer, were observed The synthesis of the target compounds was achieved using (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylic acid 4,5-di-Me ester as a chiral source. The title compounds thus formed included a maacrolactone (macrolide) (I) and related substances.
European Journal of Organic Chemistry published new progress about 4141-48-4. 4141-48-4 belongs to catalysis-chemistry, auxiliary class Aryl phosphine ligand,Mono-phosphine Ligands, name is Allyldiphenylphosphine oxide, and the molecular formula is C15H15OP, Name: Allyldiphenylphosphine oxide.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia