Total synthesis of aplyronine C
Ian Paterson1, Sarah J Fink, Lydia Y W Lee
1University Chemical Laboratory, University of Cambridge , Lensfield Road, Cambridge CB2 1EW, U.K.
Abstract:
A highly stereocontrolled total synthesis of the cytotoxic marine macrolide aplyronine C is described. The route exploits aldol methodology to install the requisite stereochemistry and features a crucial boron-mediated aldol coupling of an N-vinylformamide-bearing methyl ketone with a macrocyclic aldehyde to introduce the full side chain. The synthesis of two novel C21-C34 side chain analogs is also reported.
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