A concise synthesis of the octalactins

PT O'Sullivan, W Buhr, MAM Fuhry…

Index: 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. Journal of the American Chemical Society, 2004 , vol. 126, # 7 p. 2194 - 2207

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Citation Number: 59

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 ...