Silver carboxylate promoted lactonization: A general method applicable to prepare medium and large-sized lactones without high dilution or slow addition
Efficient and applicable approach to macrolactonizations, with ready availability of starting materials and simple operation, remains a challenging task for the organic community. We developed a 'freshman-can-do' protocol to medium- and large-sized lactones, not depending on high-dilution or slow addition techniques. Application of this method for the synthesis of natural lactones or potentially pharmaceutical compounds might be useful for organic chemists and pharmacists.
Liu, Le,Xu, Shimin,Zhou, Hongwei
supporting information
p. 8386 - 8391
(2013/09/02)
Synthesis of Macrocyclic Dilactones by Cyclization of Sulfonium Salts
An efficient method for the formation of macrocyclic dilactones via cyclization of (ω-carboxyalkyl)diphenylsulfonium salts 3 containing an ester linkage under mild conditions is described.These sulfonium salts 3 were cyclized in the presence of cesium carbonate under high-dilution conditions to give 11- to 16-membered dilactones 4 in good yields.The cyclization of sulfonium salt 22 was successfully carried out for the synthesis of 11-membered dilactonic pyrrolizidine alkaloid, 13,13-dimethyl-1,2-didehydrocrotalanine 23.