Activation of thiol esters. Partial synthesis of cytochalasins A and B

Chemistry of Acyl Radicals

“…The use of benzeneselenenyl chloride and even diphenyl diselenide in this context was alluded to in a footnote by Masamune in 1977, but no details were ever reported. 136 Grieco reported that the use of phenylselenocyanate or N-phenylselenophthalimide and tributylphosphine gave high yields of acyl selenides from carboxylic acids. 140 Crich and Batty found the use of the less expensive benzeneselenenyl chloride/tributylphosphine couple to be perfectly adequate provided that the acid is first converted to its triethylammonium salt.…”

Surface Coordination Chemistry: Corrosion Inhibition by Tetranuclear Cluster Formation of Iron with Salicylaldoxime

“…Reaction [9] of iron(iii) chloride with salicylaldoxime (H 2 SalH) [8] led to crystals formulated as [{Fe(SalH)(HSalH)} 4 ]´H 2 SalH´2 C 8 H 10 (1). [10] Compound 1 comprises two molecules of xylene, a molecule of H 2 SalH, and a cluster containing four Fe III centers, each of which has a distorted octahedral coordination environment with four O and two cis-N donor atoms (Figure 1 Elemental analyses, spectroscopic data, and other physical measurements [13] have demonstrated that the predominant constituent of the red-brown product obtained when an Fe salt reacts with salicylaldoxime is the tetranuclear cluster characterized in 1.…”

Total Synthesis of the (+)‐Antimycin A Family

“…However, as AgClO 4 salts are potentially explosive, we tested other conditions for the cyclization of thiol ester 11a. Thiol esters can be activated with copper salts as well as with silver salts [25] and the use of the copper(I) trifluoromethanesulfonate-benzene complex [(CuOTf) 2 ·PhH] led to quite a successful cyclization, giving 12a in 88 % yield when 11a was added dropwise to a 1 mmol/L solution of the complex at 80°C over 2 h (entry 4).…”