Total synthesis of (±)-sesbanimide A and B

Abstract

The total synthesis of sesbanimide A (1) and B (2) is reported which features (a) the reaction of cyclopentadiene with glyoxylic acid leading to the useful bicyclic lactone building block 3 and (b) the use of 2.5 mol dm–3 lithium perchlorate in diethyl ether to promote the conjugate addition of 1-methoxy-1-(tert-butyldimethylsiloxy)ethene to unsaturated lactone 11.