676251-79-9Relevant academic research and scientific papers
A Concise Synthesis of the Octalactins
O'Sullivan, Paul T.,Buhr, Wilm,Fuhry, Mary Ann M.,Harrison, Justin R.,Davies, John E.,Feeder, Neil,Marshall, David R.,Burton, Jonathan W.,Holmes, Andrew B.
, p. 2194 - 2207 (2004)
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 Paterson-Aldol reaction for the rapid assembly of the carbonate 46, methylenation of 46 and subsequent Claisen rearrangement of the corresponding alkenyl-substituted cyclic ketene acetal to provide the core unsaturated medium-ring lactone 47, and the use of enzyme-mediated acetate deprotection in the presence of a medium-ring lactone.
