A Concise Synthesis of the Octalactins
Journal of the American Chemical Society2004Vol. 126(7), pp. 2194–2207
Citations Over TimeTop 10% of 2004 papers
Paul T. O’Sullivan, Wilm Buhr, Mary Ann M. Fuhry, Justin R. Harrison, John E. Davies, N. Feeder, David R. Marshall, Jonathan W. Burton, Andrew B. Holmes
Abstract
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.
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