A concise synthesis of the octalactins.
作者信息
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
机构信息
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
出版信息
J Am Chem Soc. 2004 Feb 25;126(7):2194-207. doi: 10.1021/ja038353w.
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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