Bio-inspired synthesis of xishacorenes A, B, and C, and a new congener from fuscol.
- Author(s): Rovira, Alexander R;
- Müller, Nicolas;
- Deng, Weiwen;
- Ndubaku, Chudi;
- Sarpong, Richmond
- et al.
Published Web Locationhttps://doi.org/10.1039/c9sc02572c
The xishacorene natural products are structurally unique apolar diterpenoids that feature a bicyclo[3.3.1] framework. These secondary metabolites likely arise from the well-studied, structurally related diterpenoid fuscol. In this manuscript, we describe the conversion of fuscol to xishacorenes A, B, and C, as well as a previously unreported congener, which we have named xishacorene D. In addition, we describe immunomodulatory activity studies of the xishacorenes, a structurally related analogue, and fuscol. These studies were aided by an accurate determination of the physical properties (e.g., molar extinction coefficient) of the highly apolar xishacorenes.