Given these structural objec=ves, we designed a synthe=c route that leverages α-hydroxyla=on of the TCOcarboxylic acid ester 2 for introducing the direc=ng OH and -upon saponifica=on and acetyla=onsubsequent iodolactoniza=on to introduce the OH in release posi=on, trans to the direc=ng group (Fig. ). The synthesis targets the forma=on of a single diastereomer prior to flow photoisomeriza=on, minimizing the number of TCO diastereomers and facilita=ng subsequent isola=on and purifica=on.