Total synthesis of methyl 14-hydroxy-(all-cis)-5,8,11-tetradecatrienoate: A useful intermediate for the synthesis of arachidonic acid analogues

Are Alkyne Reductions Chemo-, Regio-, and Stereoselective Enough To Provide Pure (Z)-Olefins in Polyfunctionalized Bioactive Molecules?

“…Nowadays, with the Lindlar catalyst, the Brown catalyst is the most often used reducing system for the semihydrogenation of alkynes, tolerating alkenes, amides, acetal, , oxazole, benzyl group, silylated ether, , and free hydroxyl groups. , Further comments on P2–Ni catalyzed hydrogenations are given in section 3.3.…”

“…Nowadays it is widely used for achieving high stereo-, chemo-, and regioselectivity. Thus, as for the Lindlar catalyst, the Brown system has shown its appealing potential for the partial reduction of skipped dienes, − ,,,,− trienes, ,,,− and tetraenes, , mostly for PUFAs ,,, and pheromone syntheses.…”

Efficient Construction of the Bicyclo[5.3.0]decenone Skeleton Based on the Rh(I)-Catalyzed Allenic Pauson−Khand Reaction

“…1-Iodo-5-[(tetrahydro-2 H -pyran-2-yl)oxy]-3-pentyne (24). To a solution of 5-[(tetrahydro-2 H -pyran-2-yl)oxy]-3-pentyn-1-ol (800 mg, 4.4 mmol) in dry CH 2 Cl 2 (40 mL) were added PPh 3 (1.4 g, 5.3 mmol) and imidazole (360 mg, 5.3 mmol) at room temperature. Then, I 2 was added to the reaction mixture, which was stirred for 30 min.…”