Bollikonda, Satyanarayana; Mohanarangam, Saravanan; Jinna, Rajender Reddy; Kandirelli, Venkata Kiran Kumar; Makthala, Laxman; Sen, Saikat; Chaplin, David A.; Lloyd, Richard C.; Mahoney, Thomas; Dahanukar, Vilas Hareshwar; Oruganti, Srinivas; Fox, Martin E. published the artcile< An Enantioselective Formal Synthesis of Montelukast Sodium>, Safety of (9Z,12Z)-Methyl octadeca-9,12-dienoate, the main research area is montelukast sodium enantioselective formal synthesis; Mizoroki Heck double bond isomerization asym hydrogenation.
A formal synthesis of the antiasthma drug montelukast sodium is described, wherein the key chiral diol intermediate I was accessed with greater convergence of the C-C bond-forming steps as compared to previous routes. Improved synthetic efficiency was achieved by deploying homogeneous metal-based catalysis in two pivotal steps. In the first, a tandem Mizoroki-Heck reaction and double-bond isomerization between a previously known allyl alc. intermediate and a hindered 2-(2-halophenyl)propan-2-ol secured direct access to the 3-(2-(2-hydroxypropan-2-yl)phenyl)-1-phenylpropan-1-one moiety in the product. In the second step, asym. hydrogenation of the ketone functionality in the Mizoroki-Heck reaction product provided a convenient method to introduce the benzylic alc. chiral center and obtain the desired chiral diol precursor of montelukast sodium. A detailed catalyst screening led to the identification of ((R)-Xyl-BINAP)((R,R)-DPEN)RuCl2 as a catalyst that afforded an enantioselectivity of 99% ee in the hydrogenation step on a multigram lab scale at a molar substrate:catalyst loading of 5000:1.
Journal of Organic Chemistry published new progress about Enantioselective synthesis. 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Safety of (9Z,12Z)-Methyl octadeca-9,12-dienoate.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics