Synthesis of bastadin analogs through an SN Ar coupling strategy

KL Bailey, TF Molinski

Index: Bailey, Karl L.; Molinski, Tadeusz F. Tetrahedron Letters, 2002 , vol. 43, # 52 p. 9657 - 9661

Full Text: HTML

Citation Number: 13

Abstract

The synthesis of a bastadin-5 analog was achieved in 16% overall yield (16 steps, longest linear sequence) using a strategy of intermolecular SNAr coupling to create diphenyl ether bonds and sequential amide couplings to close the ring. Noteworthy elements include assembly of all four substituted aryl rings from two simple benzaldehydes, strict regiocontrol of meta-versus para-aryl ether bonds and management of the reductively-sensitive aryl ...