Abstract:

The first study describes the conversion of sclareolide to C2-functionalized lissoclimide derivatives via key C–H functionalization and asymmetric Evans aldol addition steps. The selectivity of C–H functionalization at the C2 position of sclareolide using various approached is discussed. Additionally, halogen-π interactions within the 80S ribosomal pocket were investigated for all of the novel lissoclimide derivatives.

The second study was aimed at synthesizing the trans/syn/trans-perhydrophenanthrene core of brasilicardin A via a bioinspired polyene cyclization. Epoxypolyene substrates featuring diene and enone terminating groups were constructed via a convergent B-alkyl Suzuki–Miyaura cross-coupling. Both cationic and radical polyene cyclization pathways were investigated. The results indicate that the C2 hydroxyl group is crucial for the success of the radical cyclization process.