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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.
Abstract

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.

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