A Concise Synthesis of the Octalactins Paul T. O'Sullivan Wilm Buhr Mary Ann M. Fuhry Justin R. Harrison John E. Davies Neil Feeder David R. Marshall Jonathan W. Burton Andrew B. Holmes 10.1021/ja038353w.s003 https://acs.figshare.com/articles/dataset/A_Concise_Synthesis_of_the_Octalactins/3348652 The total synthesis of octalactins A and B has been achieved in 15 steps (longest linear sequence) and 10% overall yield from commercially available materials. Key steps include the Patersonāˆ’Aldol reaction for the rapid assembly of the carbonate <b>46</b>, methylenation of <b>46</b> and subsequent Claisen rearrangement of the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ring lactone <b>47</b>, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone. 2004-02-25 00:00:00 Concise Synthesis acetate presence Paterson ketene Claisen rearrangement Key steps sequence methylenation acetal Octalactin core assembly deprotection material 15 steps octalactin lactone cyclic carbonate 46 synthesis