Total synthesis and stability analysis of natural diacyl-type tuliposides and their non-natural isomers

Tuliposides (Pos), major secondary metabolites in tulip, are classified into monoacyl- and diacyl-type compounds. Herein, we report the first total synthesis of naturally occurring diacyl-type PosD and PosF and their isomers diOH-PosD and isoPosF, respectively, from D-glucose in five steps. Under neutral conditions, the non-natural Pos isomers were significantly less stable than their natural counterparts.