Mild acetal cleavage using B-chlorocatecholborane in the synthesis of rearrangement-sensitive 2-arachidonoylglycerol
Roche, M., Madren, S. M., Tallent, C. R., Carroll, F., & Seltzman, H. (2012). Mild acetal cleavage using B-chlorocatecholborane in the synthesis of rearrangement-sensitive 2-arachidonoylglycerol. Tetrahedron Letters, 53(30), 3825-3827. DOI: 10.1016/j.tetlet.2012.04.039
A mild method for the cleavage of an acetal to afford a rearrangement sensitive diol using B-chlorocatecholborane was developed for the synthesis of the endogenous cannabinoid neurochemical messenger 2-arachidonoylglycerol. The tendency for rearrangement of 2-arachidonoylglycerol to the corresponding 1-arachidonoylglycerol was precluded with this reagent. Features of the partial recyclization to an isomeric acetal provide mechanistic detail.