Synthesis of Norleucosceptroids A, B, and K

Key words

sesterterpenoids - antifeedants - leucosceptroids

Significance

The target compounds represent a family of sesterterpenoids with antifeedant activity against a variety of plant-feeding insects and pathogens. Their potential application in plant protection renders them highly interesting targets for total synthesis and biological profiling.

Comment

The authors employed an interesting aldol-type condensation of dilactol F en route to G. H was subjected to a sequence including epoxidation followed by aluminum-mediated opening leading to the required syn-configured species I, which was elaborated into the unnatural enantiomers of norleucosceptoids A, B, and K.