Sitolactone is an inexpensive, commercially available compound featuring a trans-hydrindane ring system fused to a δlactone. Despite its important applications in the pharmaceutical industry, this compound remains strikingly underexploited in natural product synthesis. In contrast to the widely used Hajos-Parrish ketone, only four total syntheses have employed sitolactone as a starting material. This account summarizes the background and synthetic applications of sitolactone, highlighting its considerable potential as a chiral pool material worthy of greater attention from the synthetic community.
Xiao et al. (Mon,) studied this question.